(R)-1-Phenyl-2-propanol (P2Pol) [C9H12O] by Asch

Query 1. Query

Query

Results

Date

RX.PXRN=3195620

80 reactions in Reaxys

2018-05-22 18h:58m:14s (UTC)

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Rx-ID: 3756858 View in Reaxys 1/80 Yield

Conditions & References With methanesulfonic acid, (R,R)-dihydroborate in hexane, Time= 48h, T= -20 °C , Title compound not separated from byproducts Imai, Toshiro; Tamura, Tadashi; Yamamuro, Akira; Sato, Tsuneo; Wollmann, Theodor A.; et al.; Journal of the American Chemical Society; vol. 108; nb. 23; (1986); p. 7402 - 7404 View in Reaxys With nicotinamide adenine dinucleotide, rat liver homogenate supernatant, T= 37 °C , other catalysts, Product distribution Prelusky; Coutts; Pasutto; Journal of Pharmaceutical Sciences; vol. 71; nb. 12; (1982); p. 1390 - 1393 View in Reaxys With lithium aluminium tetrahydride, crowned 2,2'-dihydroxy-1,1'-binaphthyl (S,S)-4 in tetrahydrofuran, Time= 24h, T= 0 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Yamamoto, Koji; Ueno, Koji; Naemura, Koichiro; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); nb. 4; (1991); p. 2607 - 2608 View in Reaxys With water, isopropyl alcohol, T= 30 °C , resting cells of Sulfolobus solfataricus, pH 5.0, Title compound not separated from byproducts Trincone, Antonio; Nicolaus, Barbara; Lama, Licia; Gambacorta, Agata; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 32; nb. 1; (1993); p. 25 - 29 View in Reaxys With (S)-oxazaborolidine, borane in tetrahydrofuran, Time= 0.166667h, T= 25 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Kim, Yong Hae; Park, Doo Han; Byun, Il Suk; Yoon, I. K.; Park, C. S.; Journal of Organic Chemistry; vol. 58; nb. 17; (1993); p. 4511 - 4512 View in Reaxys With dimethylsulfide borane complex, (R)-B-methyl-4,5,5-triphenyl-1,3,2-oxazaborolidine in tetrahydrofuran, T= 0 °C , Title compound not separated from byproducts Berenguer; Garcia; Vilarrasa; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 165 - 168 View in Reaxys With diisobutylaluminium hydride, (S)-1-methyl-2-lt;(piperidin-1-yl)-methylgt;pyrrolidine, tin(ll) chloride in dichloromethane, Time= 0.166667h, T= -100 °C , Yield given. Yields of byproduct given Oriyama, Takeshi; Mukaiyama, Teruaki; Chemistry Letters; (1984); p. 2071 - 2074 View in Reaxys With borane-THF, L-proline in toluene, Time= 0.25h, Heating, Yield given. Yields of byproduct given. Title compound not separated from byproducts Brunel, Jean Michel; Maffei, Michel; Buono, Gerard; Tetrahedron: Asymmetry; vol. 4; nb. 10; (1993); p. 2255 - 2260 View in Reaxys With dimethylsulfide borane complex, chiral oxazaphospholidine oxide in tetrahydrofuran, T= 60 °C , Yield given. Yields of byproduct given Chiodi, Olivier; Fotiadu, Frederic; Sylvestre, Maud; Buono, Gerard; Tetrahedron Letters; vol. 37; nb. 1; (1996); p. 39 - 42 View in Reaxys With D-glucose, Zygosaccharomyces rouxii cells in water, Time= 1h, T= 28 °C

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Erdelyi, Balazs; Szabo, Antal; Seres, Gabor; Birincsik, Laszlo; Ivanics, Jozsef; Szatzker, Gabor; Poppe, Laszlo; Tetrahedron Asymmetry; vol. 17; nb. 2; (2006); p. 268 - 274 View in Reaxys With Geotrichum candidum IFO 4597 in water, Time= 24h, T= 30 °C , Microbiological reaction, Reduction, Product distribution, Further Variations: Reagents Nakamura, Kaoru; Fujii, Mikio; Ida, Yoshiteru; Journal of the Chemical Society, Perkin Transactions 1; nb. 19; (2000); p. 3205 - 3211 View in Reaxys With NADP, isopropyl alcohol in hexane, Time= 12h, T= 50 °C , Enzymatic reaction, Product distribution, Further Variations: Solvents Musa, Musa M.; Ziegelmann-Fjeld, Karla I.; Vieille, Claire; Zeikus, J. Gregory; Phillips, Robert S.; Angewandte Chemie International Edition; vol. 46; nb. 17; (2007); p. 3091 - 3094 View in Reaxys With nicotinamide adenine dinucleotide phosphate, tris hydrochloride, isopropyl alcohol in water, acetonitrile, Time= 24h, T= 50 °C , stereoselective reaction Musa, Musa M.; Ziegelmann-Fjeld, Karla I.; Vieille, Claire; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 6; nb. 5; (2008); p. 887 - 892 View in Reaxys With ECOENG500, [RuCl(p-cymene)TsDPEN], water, sodium formate, T= 20 - 50 °C , optical yield given as percent ee Hut'ka, Martin; Toma, Stefan; Monatshefte fur Chemie; vol. 139; nb. 7; (2008); p. 793 - 798 View in Reaxys With dimethylsulfide borane complex, (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole in tetrahydrofuran, Time= 14.5h, T= 30 °C , optical yield given as percent ee, enantioselective reaction Ema, Tadashi; Ura, Norichika; Yoshii, Masataka; Korenaga, Toshinobu; Sakai, Takashi; Tetrahedron; vol. 65; nb. 46; (2009); p. 9583 - 9591 View in Reaxys Stage 1: With phenylsilane, copper diacetate, (S)-4-phenyl-4,5-dihydro-3H-dinaphtholt;2,1-c;1',2'-egt;phosphepine in toluene, Time= 5h, T= -20 °C , Inert atmosphere Stage 2: With methanol, tetrabutyl ammonium fluoride in tetrahydrofuran, Time= 2h, optical yield given as percent ee, enantioselective reaction Junge, Kathrin; Wendt, Bianca; Addis, Daniele; Zhou, Shaolin; Das, Shoubhik; Beller, Matthias; Chemistry - A European Journal; vol. 16; nb. 1; (2010); p. 68 - 73 View in Reaxys General procedure for catalytic reductions: General procedure: In a Schlenk tube, dichloro-p-cymene ruthenium dimer (15.5 mg, 0.025 mmol) and ligand (0.05 mmol) were dissolved in water (4 mL) at 30°C and stirred during 1h. Sodium formate (0.68 mg, 10 mmol) and substrate (1 mmol) were then added. The reaction mixture was maintained at 30°C until total reduction of the ketone (monitored by GC). Alcohol was extracted with pentane (3x10 mL), dried over MgSO4 and evaporated under reduced pressure. The product was purified by thin layer chromatography with petroleum ether/ethyl acetate mixture, and spectral data compared with the literature[ii]. Enantiomeric excesses were determined by GC on chiral column. With (p-cymene)ruthenium(II) chloride, water, sodium formate, (2S)-N-phenylpyrrolidine-2-carboxamide, Time= 17h, T= 30 °C , Inert atmosphere, optical yield given as percent ee, enantioselective reaction Boukachabia, Mourad; Zeror, Saoussen; Collin, Jacqueline; Fiaud, Jean-Claude; Zouioueche, Louisa Aribi; Tetrahedron Letters; vol. 52; nb. 13; (2011); p. 1485 - 1489 View in Reaxys Reaction Steps: 2 1.1: iron(II) acetate; 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene / tetrahydrofuran / 65 °C / Inert atmosphere 1.2: 42 h / 20 °C / Inert atmosphere 2.1: water; sodium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C / Inert atmosphere

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With water, iron(II) acetate, 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene, sodium hydroxide in tetrahydrofuran, methanol Addis, Daniele; Shaikh, Nadim; Zhou, Shaolin; Das, Shoubhik; Junge, Kathrin; Beller, Matthius; Chemistry - An Asian Journal; vol. 5; nb. 7; (2010); p. 1687 - 1691 View in Reaxys Stage 1: With diethylzinc, 2,6-bis((R)-4-phenyl-4,5-dihydrooxazol-2-yl)pyridine in tetrahydrofuran, toluene, Time= 20h, T= 20 °C , Inert atmosphere Stage 2: With sodium hydroxide in tetrahydrofuran, methanol, diethyl ether, toluene, Time= 0.5h, Inert atmosphere, optical yield given as percent ee, enantioselective reaction Junge, Kathrin; Moeller, Konstanze; Wendt, Bianca; Das, Shoubhik; Goerdes, Dirk; Thurow, Kerstin; Beller, Matthias; Chemistry - An Asian Journal; vol. 7; nb. 2; (2012); p. 314 - 320 View in Reaxys 25 :General procedure: The hydrogenation substrate (20 mmol), the base (as in Table 2), iso-propanol (10 ml), and the catalyst precursor RuCl2(L4) (0.01 mmol) were placed into a pressure reactor and stirred under H2 (50 bar) at the given temperature for the given amount of time as indicated in Table 2. With RuCl2((R,R)-N,N'-bis(2-(tert-butylthio)-4-tert-butylbenzylidene)-1,2-diaminocyclohexane), hydrogen, potassium hydoxide in isopropyl alcohol, Time= 2.5h, T= 60 °C , p= 37503.8Torr , Inert atmosphere, Autoclave, Temperature, Reagent/catalyst, Overall yield = 99 percentChromat.; Optical yield = 40 percent ee Patent; FIRMENICH SA; Santoro, Francesco; Saudan, Lionel; Saudan, Christophe; US2013/274487; (2013); (A1) English View in Reaxys 11 : Example 11: Application of chiral spiro-pyridylamidophosphine ligand (R)-Ii (prepared in Example 9) in the asymmetric catalytic hydrogenation reaction of carbonyl compounds Example 11: Application of chiral spiro-pyridylamidophosphine ligand (R)-Ii (prepared in Example 9) in the asymmetric catalytic hydrogenation reaction of carbonyl compounds[0059] [0060] Under the protection of nitrogen atmosphere, 0.5 mg (0.74µmol) [Ir(COD)]Cl2, 1.2 mg (1.6µmol) (R)-Ii were added to the inner hydrogenation tube. Subsequently, 1 ml absolute ethyl alcohol was added and stirred for 1 h at room temperature. The inner reaction tube was placed into the hydrogenation reactor. After substitution by hydrogen, the reaction was stirred for 1 h at a hydrogen pressure of 1 atmosphere. The reactor was opened, and 7.5-150 mmol substrate (solid substrate, added after dissolved by ethanol) was added, followed by 0.05-25 mmol potassium tert-butoxide solution in ethanol (0.5 ml (0.1 mmol/mL)-25 ml (1 mmol/mL)) added with a syringe. The reactor was sealed, and hydrogen was filled to a pressure of 8-10 atm, and the reaction was stirred under the hydrogen pressure at room temperature for a while ranging from 10 minutes to 24 hours. After the hydrogenation was finished, the reaction solution was filtered through a short silica gel column to remove the catalyst, and the conversion rate and yield of the reaction were analyzed by gas chromatography or nuclear magnetic resonance (NMR); and the optical purity of the product was analyzed by gas chromatography or high performance liquid chromatography. The results of the hydrogenation experiments were listed in Table 1. With bis(1,5-cyclooctadiene)diiridium(I) dichloride, (R)-N-(3-methylpyridyl-2-methyl)-7-di-(3,5-di-tert-butylphenyl)phosphino-7'-amino-1,1'-spiro-dihydro-indene, potassium tert-butylate, hydrogen in ethanol, Time= 3h, T= 20 °C , p= 6080.41 7600.51Torr , Inert atmosphere, Sealed tube, Overall yield = 100 percent Patent; Zhejiang Jiuzhou Pharma Science and Technology Co., Ltd.; ZHOU, Qilin; XIE, Jianhua; LIU, Xiaoyan; XIE, Jianbo; WANG, Lixin; EP2641910; (2013); (A1) English View in Reaxys Asymmetric Reduction of Acetophenone with Catalyst 1;Typical Procedure General procedure: A 100 mL, flame-dried, two-necked, round-bottomed flaskequipped with a magnetic stirrer bar, was charged withcatalyst 1 (0.4 mmol) and anhyd THF (4 mL). BH3·THF (2.4mmol, 1.2 equiv) was added under argon from a syringe. Asoln of PhCOMe (2 mmol, 0.22 mL) in anhyd THF (2 mL)was added dropwise at 1 mL/h and the solution was thenstirred at r.t. under argon for 18 h. When the reaction wascomplete, the mixture was hydrolyzed by the addition ofMeOH (5 mL) and 1 M aq HCl (5 mL) and stirred for 30 min.The mixture was then extracted with Et2O (3 × 50 mL), and the combined organic extracts were dried (MgSO4) andconcentrated under reduced pressure. The residual crudeproduct was purified by column chromatography [silica gel,EtOAc–hexanes (1:3)] to give enantiomerically enriched1-phenylethanol as a colorless oil; yield: 0.17 g (70percent). With borane-THF, (2R)-2-amino-2-phenylethanol N-borane in tetrahydrofuran, Time= 18h, T= 20 °C , Inert atmosphere, Overall yield = 60 percent; enantioselective reaction

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Pinaka, Afroditi; Dimotikali, Dimitra; Chankvetadze, Bezhan; Papadopoulos, Kyriakos; Vougioukalakis, Georgios C.; Synlett; vol. 24; nb. 18; (2013); p. 2401 - 2406; Art.No: ST-2013-B0829-L View in Reaxys With secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A mutant, nicotinamide adenine dinucleotide phosphate in isopropyl alcohol, Time= 6h, T= 50 °C , pH= 8, Enzymatic reaction, enantioselective reaction Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys 11 : Example 11 Application of Chiral Spiro-Pyridylamidophosphine Ligand (R)-Ii (Prepared in Example 9) in the Asymmetric Catalytic Hydrogenation Reaction of Carbonyl Compounds Example 11 Application of Chiral Spiro-Pyridylamidophosphine Ligand (R)-Ii (Prepared in Example 9) in the Asymmetric Catalytic Hydrogenation Reaction of Carbonyl Compounds Under the protection of nitrogen atmosphere, 0.5 mg (0.74 gmol) [Ir(COD)]Cl2, 1.2 mg (1.6 μmol) (R)-Ii were added to the inner hydrogenation tube. Subsequently, 1 ml absolute ethyl alcohol was added and stirred for 1 h at room temperature. The inner reaction tube was placed into the hydrogenation reactor. After substitution by hydrogen, the reaction was stirred for 1 h at a hydrogen pressure of 1 atmosphere. The reactor was opened, and 7.5-150 mmol substrate (solid substrate, added after dissolved by ethanol) was added, followed by 0.05-25 mmol potassium tertbutoxide solution in ethanol (0.5 ml (0.1 mmol/mL)-25 ml (1 mmol/mL)) added with a syringe. The reactor was sealed, and hydrogen was filled to a pressure of 8-10 atm, and the reaction was stirred under the hydrogen pressure at room temperature for a while ranging from 10 minutes to 24 hours. After the hydrogenation was finished, the reaction solution was filtered through a short silica gel column to remove the catalyst, and the conversion rate and yield of the reaction were analyzed by gas chromatography or nuclear magnetic resonance (NMR); and the optical purity of the product was analyzed by gas chromatography or high performance liquid chromatography. The results of the hydrogenation experiments were listed in Table 1. With bis(1,5-cyclooctadiene)diiridium(I) dichloride, (R)-N-(3-methylpyridyl-2-methyl)-7-di-(3,5-di-tert-butylphenyl)phosphino-7'-amino-1,1'-spiro-dihydro-indene, potassium tert-butylate, hydrogen in ethanol, Time= 3h, T= 20 °C , p= 6080.41 7600.51Torr , Autoclave, Overall yield = 100percent; Optical yield = 25percent ee Patent; Zhejiang Jiuzhou Pharma Science and Technology Co., Ltd.; Zhou, Qilin; Xie, Jianhua; Liu, Xiaoyan; Xie, Jianbo; Wang, Lixin; US8962839; (2015); (B2) English View in Reaxys Stage 1: With diethoxymethylane, C36H31FeN3O3 in toluene, Time= 6h, T= -78 - 20 °C , Schlenk technique, Inert atmosphere Stage 2: With potassium carbonate in methanol, Time= 1h, T= 20 °C , Schlenk technique, Inert atmosphere, enantioselective reaction Bleith, Tim; Wadepohl, Hubert; Gade, Lutz H.; Journal of the American Chemical Society; vol. 137; nb. 7; (2015); p. 2456 2459 View in Reaxys 2.2.2. General procedure for mutant TeSADH-catalyzed racemization General procedure: Enantiopure alcohol (0.015 mmol), NADP+ (0.5 mg), NADPH (1.0 mg), mutant TeSADH (0.2 mg in Tris– HCl buffer solution, 50 mM, pH 8.0), Tris–HCl buffer solution (950 μL, 50 mM, pH 8.0), and acetonitrile (50 μL) were mixed in a 1.5-mL plastic tube. The reaction mixture was shaken at 50 °C and 200 rpm for 48 h, followed by extraction with ethyl acetate (2 × 500 μL). The combined organic layer was dried with sodium sulfate and concentrated to dryness. The remaining residue was treated with pyridine (two drops) and acetic anhydride (one drop) for 1 h to convert the alcohols to their corresponding acetates. The acetate products were diluted with CHCl3 prior to analysis on a GC equipped with a chiral column to determine ee. With NADPH, nicotinamide adenine dinucleotide phosphate, W110A TeSADH in acetonitrile, T= 50 °C , pH= 8, Enzymatic reaction Musa, Musa M.; Patel, Jay M.; Nealon, Christopher M.; Kim, Chang Sup; Phillips, Robert S.; Karume, Ibrahim; Journal of Molecular Catalysis B: Enzymatic; vol. 115; (2015); p. 155 - 159 View in Reaxys 2.2.2. General procedure for mutant TeSADH-catalyzed racemization General procedure: Enantiopure alcohol (0.015 mmol), NADP+ (0.5 mg), NADPH (1.0 mg), mutant TeSADH (0.2 mg in Tris– HCl buffer solution, 50 mM, pH 8.0), Tris–HCl buffer solution (950 μL, 50 mM, pH 8.0), and acetonitrile (50 μL) were mixed in a 1.5-mL plastic tube. The reaction mixture was shaken at 50 °C and 200 rpm for 48 h, followed by extraction with ethyl acetate (2 × 500 μL). The combined organic layer was dried with sodium sulfate and concentrated to dryness. The remaining residue

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was treated with pyridine (two drops) and acetic anhydride (one drop) for 1 h to convert the alcohols to their corresponding acetates. The acetate products were diluted with CHCl3 prior to analysis on a GC equipped with a chiral column to determine ee. With NADPH, nicotinamide adenine dinucleotide phosphate, W110G TeSADH in acetonitrile, T= 50 °C , pH= 8, Enzymatic reaction Musa, Musa M.; Patel, Jay M.; Nealon, Christopher M.; Kim, Chang Sup; Phillips, Robert S.; Karume, Ibrahim; Journal of Molecular Catalysis B: Enzymatic; vol. 115; (2015); p. 155 - 159 View in Reaxys With Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110A mutant, NADP in isopropyl alcohol, acetone, Time= 24h, T= 50 °C , pH= 8, Enzymatic reaction, enantioselective reaction Karume, Ibrahim; Takahashi, Masateru; Hamdan, Samir M.; Musa, Musa M.; ChemCatChem; vol. 8; nb. 8; (2016); p. 1459 - 1463 View in Reaxys With Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110G mutant, NADP in isopropyl alcohol, acetone, Time= 24h, T= 50 °C , pH= 8, Enzymatic reaction, enantioselective reaction Karume, Ibrahim; Takahashi, Masateru; Hamdan, Samir M.; Musa, Musa M.; ChemCatChem; vol. 8; nb. 8; (2016); p. 1459 - 1463 View in Reaxys Typical preparative scalereactions using TbSADH best mutant General procedure: A test tube (10 mL)containing LB (4 mL) and kanamycin (50 µg/mL) was inoculated with mutant SZ2074 and incubated 8h (37°C, 220 rpm). The pre-culture was then inoculated intoTB (400 mL) containing kanamycin (50 µg/mL) and allowed to grow at 37°C until O.D.was ca. 0.6. IPTG was then added to a final concentration of 0.2 mM and theculture was grown for 16 h (30°C, 180 rpm). Cells were pelleted bycentrifugation, washed once with pH=7.4 potassium phosphate buffer (100 mM) andthen resuspended in pH=7.4 potassium phosphate buffer (45 mL, 100 mM). Cellswere then transferred to a 50 mL Erlenmeyer flask and 1.4 mg/mL lysozyme (70mg), 6U DNase I (50 µL), NADP+ 100mM (200 µL) were added. Substrate 3a (30 mM) in 10percent isopropanol (5 mL)was then added. Biotransformation was carried out at 30°C, 220rpm. GC controlindicated a 92percent conversion after 4h. The reaction was stopped after 6h when theconversion was 94percent. The organic phase was extracted with ethyl acetate (3x100mL) and crude reaction product was purified using column chromatography. (EA:PE1:4, Rf=0.55) afforded (R)-4a as a colourless liquid (157 mg,yield=75percent). With alcohol dehydrogenase TbSADH from Thermoanaerobacter brockii A85V/I86L/W110Q/L294Q mutant in aq. phosphate buffer, isopropyl alcohol, T= 30 °C , Enzymatic reaction, Reagent/catalyst, enantioselective reaction Sun, Zhoutong; Li, Guangyue; Ilie, Adriana; Reetz, Manfred T.; Tetrahedron Letters; vol. 57; nb. 32; (2016); p. 3648 - 3651 View in Reaxys Typical preparative scalereactions using TbSADH best mutant General procedure: A test tube (10 mL)containing LB (4 mL) and kanamycin (50 µg/mL) was inoculated with mutant SZ2074 and incubated 8h (37°C, 220 rpm). The pre-culture was then inoculated intoTB (400 mL) containing kanamycin (50 µg/mL) and allowed to grow at 37°C until O.D.was ca. 0.6. IPTG was then added to a final concentration of 0.2 mM and theculture was grown for 16 h (30°C, 180 rpm). Cells were pelleted bycentrifugation, washed once with pH=7.4 potassium phosphate buffer (100 mM) andthen resuspended in pH=7.4 potassium phosphate buffer (45 mL, 100 mM). Cellswere then transferred to a 50 mL Erlenmeyer flask and 1.4 mg/mL lysozyme (70mg), 6U DNase I (50 µL), NADP+ 100mM (200 µL) were added. Substrate 3a (30 mM) in 10percent isopropanol (5 mL)was then added. Biotransformation was carried out at 30°C, 220rpm. GC controlindicated a 92percent conversion after 4h. The reaction was stopped after 6h when theconversion was 94percent. The organic phase was extracted with ethyl acetate (3x100mL) and crude reaction product was purified using column chromatography. (EA:PE1:4, Rf=0.55) afforded (R)-4a as a colourless liquid (157 mg,yield=75percent). With alcohol dehydrogenase TbSADH from Thermoanaerobacter brockii I86N mutant in aq. phosphate buffer, isopropyl alcohol, T= 30 °C , Enzymatic reaction, Reagent/catalyst, enantioselective reaction Sun, Zhoutong; Li, Guangyue; Ilie, Adriana; Reetz, Manfred T.; Tetrahedron Letters; vol. 57; nb. 32; (2016); p. 3648 - 3651 View in Reaxys With D-glucose in isopropyl alcohol, Time= 6h, T= 30 °C , pH= 7.5, Enzymatic reaction, Solvent, Reagent/catalyst, stereoselective reaction

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Bódai, Viktória; Nagy-Győr, László; Örkényi, Róbert; Molnár, Zsófia; Kohári, Szabolcs; Erdélyi, Balázs; Nagymáté, Zsuzsanna; Romsics, Csaba; Paizs, Csaba; Poppe, László; Hornyánszky, Gábor; Journal of Molecular Catalysis B: Enzymatic; vol. 134; (2016); p. 206 - 214 View in Reaxys With D-fructose, choline chloride, Time= 144h, T= 37 °C , Reagent/catalyst, Solvent, Overall yield = 88 percent Vitale, Paola; Abbinante, Vincenzo Mirco; Perna, Filippo Maria; Salomone, Antonio; Cardellicchio, Cosimo; Capriati, Vito; Advanced Synthesis and Catalysis; vol. 359; nb. 6; (2017); p. 1049 - 1057 View in Reaxys With choline chloride in water, glycerol, Time= 120h, T= 37 °C , Reagent/catalyst, Overall yield = 20 percent Vitale, Paola; Abbinante, Vincenzo Mirco; Perna, Filippo Maria; Salomone, Antonio; Cardellicchio, Cosimo; Capriati, Vito; Advanced Synthesis and Catalysis; vol. 359; nb. 6; (2017); p. 1049 - 1057 View in Reaxys With E. coli lyophilized alcohol dehydrogenase from Thermoanaerobacter ethanolicus I86A W110A variant, nicotinamide adenine dinucleotide phosphate in isopropyl alcohol, Time= 16h, T= 30 °C , pH= 7, Enzymatic reaction, enantioselective reaction Knaus, Tanja; Cariati, Luca; Masman, Marcelo F; Mutti, Francesco G.; Organic and Biomolecular Chemistry; vol. 15; nb. 39; (2017); p. 8313 - 8325 View in Reaxys With E. coli lyophilized alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A variant, nicotinamide adenine dinucleotide phosphate in isopropyl alcohol, Time= 16h, T= 30 °C , pH= 7, Enzymatic reaction, Reagent/catalyst, enantioselective reaction Knaus, Tanja; Cariati, Luca; Masman, Marcelo F; Mutti, Francesco G.; Organic and Biomolecular Chemistry; vol. 15; nb. 39; (2017); p. 8313 - 8325 View in Reaxys With NADP, alcohol dehydrogenase, Enzymatic reaction, stereoselective reaction Qu, Ge; Lonsdale, Richard; Yao, Peiyuan; Li, Guangyue; Liu, Beibei; Reetz, Manfred T.; Sun, Zhoutong; ChemBioChem; vol. 19; nb. 3; (2018); p. 239 - 246 View in Reaxys With DL-dithiothreitol, W110A/I86A double mutated thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase, nicotinamide adenine dinucleotide phosphate, isopropyl alcohol, zinc(II) chloride in aq. buffer, T= 50 °C , pH= 8, Enzymatic reaction, enantioselective reaction Musa, Musa M.; Bsharat, Odey; Karume, Ibrahim; Vieille, Claire; Takahashi, Masateru; Hamdan, Samir M.; European Journal of Organic Chemistry; vol. 2018; nb. 6; (2018); p. 798 - 805 View in Reaxys With W110A mutated thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase, nicotinamide adenine dinucleotide phosphate, isopropyl alcohol in aq. buffer, T= 50 °C , pH= 8, Enzymatic reaction, Reagent/catalyst, enantioselective reaction Musa, Musa M.; Bsharat, Odey; Karume, Ibrahim; Vieille, Claire; Takahashi, Masateru; Hamdan, Samir M.; European Journal of Organic Chemistry; vol. 2018; nb. 6; (2018); p. 798 - 805 View in Reaxys

HO O

H O

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Rx-ID: 28201976 View in Reaxys 2/80 Yield

Conditions & References With 2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine, N-ethyl-N,N-diisopropylamine in tert-Amyl alcohol, toluene, Time= 10h, T= -40 °C , optical yield given as percent ee Birman, Vladimir B.; Li, Ximin; Organic Letters; vol. 10; nb. 6; (2008); p. 1115 - 1118 View in Reaxys With (S)-(–)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole, sodium sulfate, N-ethyl-N,N-diisopropylamine in chloroform, Time= 8h, T= 0 °C , Resolution of racemate, Kinetics, Reagent/catalyst, optical yield given as percent ee, enantioselective reaction Li, Ximin; Jiang, Hui; Uffman, Eric W.; Guo, Lei; Zhang, Yuhua; Yang, Xing; Birman, Vladimir B.; Journal of Organic Chemistry; vol. 77; nb. 4; (2012); p. 1722 - 1737 View in Reaxys With N-ethyl-N,N-diisopropylamine in chloroform, Time= 16h, T= 20 °C , enantioselective reaction Neyyappadath, Rifahath Mon; Chisholm, Ross; Greenhalgh, Mark D.; Rodríguez-Escrich, Carles; Pericàs, Miquel A.; Hähner, Georg; Smith, Andrew D.; ACS Catalysis; vol. 8; nb. 2; (2018); p. 1067 - 1075 View in Reaxys

Rx-ID: 47194690 View in Reaxys 3/80 Yield

Conditions & References With Amano lipase PS from Burkholderia cepacia immobilized on covalent organic framework in hexane, Time= 0.5h, T= 45 °C , Resolution of racemate, Overall yield = 47 percent Sun, Qi; Fu, Chung-Wei; Aguila, Briana; Perman, Jason; Wang, Sai; Huang, Hsi-Ya; Xiao, Feng-Shou; Ma, Shengqian; Journal of the American Chemical Society; vol. 140; nb. 3; (2018); p. 984 - 992 View in Reaxys

Rx-ID: 3756861 View in Reaxys 4/80 Yield

Conditions & References With magnesium chloride in isopropyl alcohol, T= 25 °C , pH= 7, Catalytic behavior Benítez-Mateos, Ana I.; San Sebastian, Eneko; Ríos-Lombardía, Nicolás; Morís, Francisco; González-Sabín, Javier; López-Gallego, Fernando; Chemistry - A European Journal; vol. 23; nb. 66; (2017); p. 16843 - 16852 View in Reaxys With isopropyl alcohol, 1-butyl-3-methylimidazolium trifluoromethanesulfonimide, T= 40 °C , pH= 6, Microbiological reaction Schroer, Kirsten; Tacha, Eva; Luetz, Stephan; Organic Process Research and Development; vol. 11; nb. 5; (2007); p. 836 841 View in Reaxys With 15percent aqueous acidic TiCl3, 30percent aqueous NH3 in methanol, Time= 0.0833333h, T= 0 - 20 °C

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Clerici, Angelo; Pastori, Nadia; Porta, Ombretta; European Journal of Organic Chemistry; nb. 12; (2001); p. 2235 - 2243 View in Reaxys With choline chloride in water, glycerol, Time= 144h, T= 37 °C Vitale, Paola; Abbinante, Vincenzo Mirco; Perna, Filippo Maria; Salomone, Antonio; Cardellicchio, Cosimo; Capriati, Vito; Advanced Synthesis and Catalysis; vol. 359; nb. 6; (2017); p. 1049 - 1057 View in Reaxys With diisobutylaluminium hydride, (S)-1-methyl-2-lt;(piperidin-1-yl)-methylgt;pyrrolidine, tin(ll) chloride in dichloromethane, Time= 0.166667h, T= -100 °C , investigation of the effect of employed chiral diamine on optical yield, Product distribution Oriyama, Takeshi; Mukaiyama, Teruaki; Chemistry Letters; (1984); p. 2071 - 2074 View in Reaxys With dimethylsulfide borane complex, C11H17BNOP in toluene, Time= 0.0833333h, T= 110 °C Buono, Gerard; Brunel, Jean-Michel; Faure, Bruno; Pardigon, Olivier; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 75; nb. 1-4; (1993); p. 43 - 46 View in Reaxys Reaction Steps: 4 1: 90 percent / bakers' yeast; Tween 80; aq. sucrose / 25 - 32 °C 2: 85 percent / 4-(dimethylamino)pyridine; pyridine / 3 h / 30 °C 3: triethylamine / 3 h / 75 - 80 °C 4: aq. LiOH / methanol / 3 h / 20 °C With pyridine, dmap, lithium hydroxide, Tween 80, bakers' yeast, triethylamine, Sucrose in methanol Shi, Xiao-Xin; Yao, Jian-Zhong; Kang, Li; Shen, Chun-Li; Yi, Fei; Journal of Chemical Research; nb. 10; (2004); p. 681 683 View in Reaxys Reaction Steps: 2 1: 90 percent / SO2Cl2 / CCl4 / 40 °C 2: 24 h / Lactobacillus kefir With sulfuryl dichloride in tetrachloromethane Besse; Renard; Veschambre; Tetrahedron Asymmetry; vol. 5; nb. 7; (1994); p. 1249 - 1268 View in Reaxys Reaction Steps: 3 1: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / isopropyl alcohol / 6 h / 50 °C / pH 8 / Enzymatic reaction 2: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / aq. buffer / 50 °C / pH 8.9 / Enzymatic reaction 3: nicotinamide adenine dinucleotide phosphate; secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A mutant / isopropyl alcohol / 6 h / 50 °C / pH 8 / Enzymatic reaction With secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A mutant, secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, nicotinamide adenine dinucleotide phosphate in isopropyl alcohol Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys Typical preparative scalereactions using TbSADH best mutant General procedure: A test tube (10 mL)containing LB (4 mL) and kanamycin (50 µg/mL) was inoculated with mutant SZ2074 and incubated 8h (37°C, 220 rpm). The pre-culture was then inoculated intoTB (400 mL) containing kanamycin (50 µg/mL) and allowed to grow at 37°C until O.D.was ca. 0.6. IPTG was then added to a final concentration of 0.2 mM and theculture was grown for 16 h (30°C, 180 rpm). Cells were pelleted bycentrifugation, washed once with pH=7.4 potassium phosphate buffer (100 mM) andthen resuspended in pH=7.4 potassium phosphate buffer (45 mL, 100 mM). Cellswere then transferred to a 50 mL Erlenmeyer flask and 1.4 mg/mL lysozyme (70mg), 6U DNase I (50 µL), NADP+ 100mM (200 µL) were added. Substrate 3a (30 mM) in 10percent isopropanol (5 mL)was then added. Biotransformation was carried out at 30°C, 220rpm. GC controlindicated a 92percent conversion after 4h. The reaction was stopped after 6h when theconversion was 94percent. The organic phase

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was extracted with ethyl acetate (3x100mL) and crude reaction product was purified using column chromatography. (EA:PE1:4, Rf=0.55) afforded (R)-4a as a colourless liquid (157 mg,yield=75percent). With alcohol dehydrogenase TbSADH from Thermoanaerobacter brockii I86A mutant in aq. phosphate buffer, isopropyl alcohol, T= 30 °C , Enzymatic reaction, enantioselective reaction Sun, Zhoutong; Li, Guangyue; Ilie, Adriana; Reetz, Manfred T.; Tetrahedron Letters; vol. 57; nb. 32; (2016); p. 3648 - 3651 View in Reaxys

Rx-ID: 8618016 View in Reaxys 5/80 Yield

Conditions & References With vinyl acetate, subtilisin in di-isopropyl ether, T= 10 - 40 °C , resolution, Thermodynamic data Ema, Tadashi; Yamaguchi, Kunihiro; Wakasa, Yuji; Tanaka, Nobuaki; Utaka, Masanori; Sakai, Takashi; Chemistry Letters; nb. 7; (2000); p. 782 - 783 View in Reaxys With MCCD-HPS packed column in hydrogenchloride, acetonitrile, pH= 8.6 Gong, Yinhan; Lee, Hian Kee; Analytical Chemistry; vol. 75; nb. 6; (2003); p. 1348 - 1354 View in Reaxys General procedure: Gas chromatographicmeasurements were performed on a GC-14B (Shimadzu, Japan) system withflame ionization detector. Nitrogen (99.999percent) was used as the carrier gas. Aβ-DEX 225 capillary column (30 m long × 0.25 mm i.d. × 0.25 μm filmthickness, Supelco Inc.), a Chirasil L-Val capillary column (25 m long × 0.25mm i.d. × 0.12 μm film thickness, Agilent Technologies), and a Cyclosil-Bcapillary column (30 m long × 0.32 mm i.d. × 0.25 μm film thickness, AgilentTechnologies) were employed as commercial columns for comparison. With [Co2((S)-mandelate)2(4,4'-bipyridine)3](NO3)2 coated capillary column, Time= 0.0283333h, T= 150 °C , Resolution of racemate, Reagent/catalyst Zhang, Shi-Yuan; Yang, Cheng-Xiong; Shi, Wei; Yan, Xiu-Ping; Cheng, Peng; Wojtas, Lukasz; Zaworotko, Michael J.; Chem; vol. 3; nb. 2; (2017); p. 281 - 289 View in Reaxys With Chiralpak ID in hexane, isopropyl alcohol, Resolution of racemate Ahmed, Marwa; Gwairgi, Marina; Ghanem, Ashraf; Chirality; vol. 26; nb. 11; (2014); p. 677 - 682 View in Reaxys

O H

Rx-ID: 11178466 View in Reaxys 6/80 Yield

Conditions & References Stage 1: With C30H32FeNPS, Time= 5h, T= 20 °C Stage 2: With hydrogenchloride in methanol, Time= 1h, Reflux Song, Heng; Ye, Ke; Geng, Peiyu; Han, Xiao; Liao, Rongzhen; Tung, Chen-Ho; Wang, Wenguang; ACS Catalysis; vol. 7; nb. 11; (2017); p. 7709 - 7717 View in Reaxys With hydrogen, Pd/magnetite in ethyl acetate, Time= 0.7h, T= 23 °C , p= 760.051Torr

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Kwon, Min Serk; Park, In Soo; Jang, Jum Suk; Lee, Jae Sung; Park, Jaiwook; Organic Letters; vol. 9; nb. 17; (2007); p. 3417 - 3419 View in Reaxys Reaction Steps: 2 1: aq. K2CO3 / Heating 2: (i) PBr5, CHCl3, (ii) Zn-Cu, aq. HCl With potassium carbonate Fischer,F.; Chemische Berichte; vol. 94; (1961); p. 893 - 901 View in Reaxys

Rx-ID: 33198467 View in Reaxys 7/80 Yield

Conditions & References With lipase AK from Pseudomonas fluorescens in tetrahydrofuran, hexane, Time= 4h, T= 30 °C , Sealed tube, optical yield given as percent ee Weiser, Diana; Boros, Zoltan; Hornyanszky, Gabor; Toth, Alexandra; Poppe, Laszlo; Process Biochemistry; vol. 47; nb. 3; (2012); p. 428 - 434 View in Reaxys With Candida antarctica lipase B in toluene, Time= 18h, T= 30 °C , Resolution of racemate, Enzymatic reaction, Kinetics, Catalytic behavior, Concentration, Solvent, enantioselective reaction Kitamoto, Yuichi; Kuruma, Yosuke; Suzuki, Kazumi; Hattori, Tetsutaro; Journal of Organic Chemistry; vol. 80; nb. 1; (2015); p. 521 - 527 View in Reaxys 4.5 General procedure for enzymatic reaction in CO2-expanded liquids General procedure: Novozym 435, bio-based liquid, alcohol, vinyl acetate, and a magnetic bar were added and sealed in a highpressure-resistant stainless-steel vessel (10mL volume) at 20°C. CO2 gas was sent into the vessel by a CO2 pump until desired pressure was achieved. The reaction mixture was magnetically stirred. At the end of the reaction, the vessel was gradually depressurized on ice. An aliquot (20μL) was filtered through EXtrelut® and diluted with diethyl ether before being analyzed by GC or HPLC. With carbon dioxide in 2-methyltetrahydrofuran, Time= 5h, T= 20 °C , p= 45004.5Torr , Sealed tube, Resolution of racemate, Enzymatic reaction, enantioselective reaction Hoang, Hai Nam; Nagashima, Yoshihiro; Mori, Shuichi; Kagechika, Hiroyuki; Matsuda, Tomoko; Tetrahedron; vol. 73; nb. 20; (2017); p. 2984 - 2989 View in Reaxys

Rx-ID: 46613225 View in Reaxys 8/80 Yield

Conditions & References 1 : Synthesis of compound 10. (S)-3-(4-methoxyphenyl)-N-(1-phenylpropan-2-yl)propan-1-amine

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To a solution of phenyllithium (50 mL, 1.8 M in dibutyl ether) in THF (50 mL) was added (R)-propylene oxide (5 g) dropwise at −78° C. The resulting mixture was stirred at the same temperature for 1 hr before warmed to room temperature. After stirred at room temperature overnight, the reaction was quenched by adding saturated NH4Cl aqueous solution. The aqueous phase was extracted with ethyl acetate (3×50 mL) and the combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was chromatographed on silica (hexanes/ethyl acetate 10:1 to 3:1) to afford (R)-1-phenylpropan-2-ol (10.4 g) as a colorless oil. in tetrahydrofuran, dibutyl ether, Time= 1h, T= -78 °C Patent; University of Kentucky Research Foundation; DWOSKIN, Linda; CROOKS, Peter Anthony; ZHENG, Guangrong; NICKELL, Justin R.; CAO, Zheng; LEE, Na-Ra; (15 pag.); US2017/304227; (2017); (A1) English View in Reaxys

Rx-ID: 1983185 View in Reaxys 9/80 Yield

Conditions & References With air, cells of Geotrichum candidum IFO 5767 in water, Time= 24h, T= 30 °C Nakamura, Kaoru; Fujii, Mikio; Ida, Yoshiteru; Tetrahedron Asymmetry; vol. 12; nb. 22; (2001); p. 3147 - 3153 View in Reaxys Gutman, Arie L.; Brenner, Dov; Boltanski, Aviv; Tetrahedron: Asymmetry; vol. 4; nb. 5; (1993); p. 839 - 844 View in Reaxys Reaction Steps: 2 1: Burkholderia cepacia lipase immobilized on ceramic particles / hexane / 48 h / 20 °C 2: sodium hydroxide / H2O; methanol With sodium hydroxide, Burkholderia cepacia lipase immobilized on ceramic particles in methanol, hexane, water Kiss, Violetta; Egri, Gabriella; Balint, Jozsef; Ling, Istvan; Barkoczi, Jozsef; Fogassy, Elemer; Tetrahedron Asymmetry; vol. 17; nb. 15; (2006); p. 2220 - 2234 View in Reaxys Reaction Steps: 2 1: Burkholderia cepacia lipase immobilized on ceramic particles / hexane / 48 h / 20 °C 2: sodium hydroxide / H2O; methanol With sodium hydroxide, Burkholderia cepacia lipase immobilized on ceramic particles in methanol, hexane, water Kiss, Violetta; Egri, Gabriella; Balint, Jozsef; Ling, Istvan; Barkoczi, Jozsef; Fogassy, Elemer; Tetrahedron Asymmetry; vol. 17; nb. 15; (2006); p. 2220 - 2234 View in Reaxys Reaction Steps: 2 1: Burkholderia cepacia lipase immobilized on ceramic particles / tetrahydrofuran / 48 h / 20 °C 2: sodium hydroxide / H2O; methanol With sodium hydroxide, Burkholderia cepacia lipase immobilized on ceramic particles in tetrahydrofuran, methanol, water Kiss, Violetta; Egri, Gabriella; Balint, Jozsef; Ling, Istvan; Barkoczi, Jozsef; Fogassy, Elemer; Tetrahedron Asymmetry; vol. 17; nb. 15; (2006); p. 2220 - 2234 View in Reaxys Reaction Steps: 2 1.1: Candida antarctica lipase B / toluene / 20 °C 1.2: polymer-bound benzoyl chloride; Et3N; DMAP / CH2Cl2 / 20 °C 2.1: KOH / tetrahydrofuran; methanol / 12 h With Candida antarctica lipase B, potassium hydroxide in tetrahydrofuran, methanol, toluene Cordova; Tremblay; Clapham; Janda; Journal of Organic Chemistry; vol. 66; nb. 16; (2001); p. 5645 - 5648 View in Reaxys

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Reaction Steps: 2 2: 1 M ethanol. NaOH / 4 h / 25 °C With sodium hydroxide Bianchi, Daniele; Cesti, Pietro; Battistel, Ezio; Journal of Organic Chemistry; vol. 53; nb. 23; (1988); p. 5531 - 5534 View in Reaxys Reaction Steps: 2 1: benzene / 30 h / 21 °C / lipase Amano P/Celite 577 2: 1 M ethanol. NaOH / 4 h / 25 °C With sodium hydroxide in benzene Bianchi, Daniele; Cesti, Pietro; Battistel, Ezio; Journal of Organic Chemistry; vol. 53; nb. 23; (1988); p. 5531 - 5534 View in Reaxys Reaction Steps: 2 1: 39 percent / benzene / 10 h / 21 °C / lipase Amano P/Celite 577 2: 1 M ethanol. NaOH / 4 h / 25 °C With sodium hydroxide in benzene Bianchi, Daniele; Cesti, Pietro; Battistel, Ezio; Journal of Organic Chemistry; vol. 53; nb. 23; (1988); p. 5531 - 5534 View in Reaxys Reaction Steps: 2 1: Candida antarctica lipase B / toluene / 20 °C / Enzymatic reaction 2: potassium hydoxide; water / methanol With Candida antarctica lipase B, water, potassium hydoxide in methanol, toluene Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys Reaction Steps: 3 1: Candida antarctica lipase B / toluene / 20 °C / Enzymatic reaction 2: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / aq. buffer / 50 °C / pH 8.9 / Enzymatic reaction 3: nicotinamide adenine dinucleotide phosphate; secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A mutant / isopropyl alcohol / 6 h / 50 °C / pH 8 / Enzymatic reaction With Candida antarctica lipase B, secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A mutant, secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, nicotinamide adenine dinucleotide phosphate in isopropyl alcohol, toluene Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys Reaction Steps: 2 1: Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110G mutant; NADP / acetone / 24 h / 50 °C / pH 8 / Enzymatic reaction 2: Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110G mutant; NADP / acetone; isopropyl alcohol / 24 h / 50 °C / pH 8 / Enzymatic reaction With Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110G mutant, NADP in isopropyl alcohol, acetone Karume, Ibrahim; Takahashi, Masateru; Hamdan, Samir M.; Musa, Musa M.; ChemCatChem; vol. 8; nb. 8; (2016); p. 1459 - 1463 View in Reaxys

Rx-ID: 5195147 View in Reaxys 10/80

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Yield

Conditions & References

66 %

With (1R)-N-oxyl-1-(N-benzylcarbamoyl)-8-azabicyclo[3.2.1]octane, sodium hydrogencarbonate, sodium bromide in dichloromethane, water, T= 0 °C , Electrochemical reaction, optical yield given as percent ee, enantioselective reaction Demizu, Yosuke; Shiigi, Hirofumi; Mori, Hiroyuki; Matsumoto, Kazuya; Onomura, Osamu; Tetrahedron Asymmetry; vol. 19; nb. 23; (2008); p. 2659 - 2665 View in Reaxys

40 %

With Sphingomonas paucimobilis NCIMB 8195 in water, N,N-dimethyl-formamide, Time= 120h Allan; Carnell; Journal of Organic Chemistry; vol. 66; nb. 19; (2001); p. 6495 - 6497 View in Reaxys

44 % Chromat.

With Geotrichum candidum IFO 4597 cells on BL-100 polymer, cyclohexanone in hexane, Time= 24h, T= 30 °C , Oxidation Nakamura, Kaoru; Inoue, Yuko; Matsuda, Tomoko; Misawa, Ibuki; Journal of the Chemical Society - Perkin Transactions 1; nb. 16; (1999); p. 2397 - 2402 View in Reaxys

50.9 % Chromat.

With air, (R,R)-(nitroso)(salen)ruthenium(II) chloride in toluene, Time= 17h, T= 20 °C , Irradiation, resolution of racemate; oxidation Masutani, Kouta; Uchida, Tatsuya; Irie, Ryo; Katsuki, Tsutomu; Tetrahedron Letters; vol. 41; nb. 26; (2000); p. 5119 - 5123 View in Reaxys With [bis(acetoxy)iodo]benzene, tetraethylammonium bromide, [Mn{CHPhNCH[OC6H2(t-Bu)2]}2]PF6 in water, Time= 0.5h, T= 20 °C , Product distribution, Further Variations: Catalysts, reaction times Sun, Wei; Wang, Hongwang; Xia, Chungu; Li, Jingwei; Zhao, Peiqing; Angewandte Chemie - International Edition; vol. 42; nb. 9; (2003); p. 1042 - 1044 View in Reaxys With lyophilized cells of Rhodococcus ruber DSM 44541, acetone in phosphate buffer, Time= 24h, T= 24 °C , pH= 8.0, Title compound not separated from byproducts Stampfer, Wolfgang; Kosjek, Birgit; Faber, Kurt; Kroutil, Wolfgang; Journal of Organic Chemistry; vol. 68; nb. 2; (2003); p. 402 - 406 View in Reaxys With air, chiral Ru(salen)(nitrosyl) complex in chloroform, Time= 11h, T= 20 °C , UV-irradiation, Kinetics Nakamura, Yukie; Egami, Hiromichi; Matsumoto, Kazuhiro; Uchida, Tatsuya; Katsuki, Tsutomu; Tetrahedron; vol. 63; nb. 28; (2007); p. 6383 - 6387 View in Reaxys With air, chiral Ru(salen)(nitrosyl) complex in chloroform, T= 20 °C , UV-irradiation, Title compound not separated from byproducts. Nakamura, Yukie; Egami, Hiromichi; Matsumoto, Kazuhiro; Uchida, Tatsuya; Katsuki, Tsutomu; Tetrahedron; vol. 63; nb. 28; (2007); p. 6383 - 6387 View in Reaxys With Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110G mutant, NADP in acetone, Time= 24h, T= 50 °C , pH= 8, Enzymatic reaction, Reagent/catalyst, enantioselective reaction Karume, Ibrahim; Takahashi, Masateru; Hamdan, Samir M.; Musa, Musa M.; ChemCatChem; vol. 8; nb. 8; (2016); p. 1459 - 1463 View in Reaxys

Rx-ID: 13206940 View in Reaxys 11/80

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Yield

Conditions & References Reaction Steps: 3 1: 85 percent / 4-(dimethylamino)pyridine; pyridine / 3 h / 30 °C 2: triethylamine / 3 h / 75 - 80 °C 3: aq. LiOH / methanol / 3 h / 20 °C With pyridine, dmap, lithium hydroxide, triethylamine in methanol Shi, Xiao-Xin; Yao, Jian-Zhong; Kang, Li; Shen, Chun-Li; Yi, Fei; Journal of Chemical Research; nb. 10; (2004); p. 681 683 View in Reaxys With Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110A, NAD, NADPH in acetonitrile, Time= 48h, T= 50 °C , pH= 8, Enzymatic reaction, Solvent Musa, Musa M.; Phillips, Robert S.; Laivenieks, Maris; Vieille, Claire; Takahashi, Masateru; Hamdan, Samir M.; Organic and Biomolecular Chemistry; vol. 11; nb. 17; (2013); p. 2911 - 2915 View in Reaxys Reaction Steps: 2 1: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / aq. buffer / 50 °C / pH 8.9 / Enzymatic reaction 2: nicotinamide adenine dinucleotide phosphate; secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A mutant / isopropyl alcohol / 6 h / 50 °C / pH 8 / Enzymatic reaction With secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A mutant, secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, nicotinamide adenine dinucleotide phosphate in isopropyl alcohol Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys With Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110A mutant, nicotinamide adenine dinucleotide phosphate, NADPH in hexane, Time= 24h, T= 50 °C , Catalytic behavior, Solvent Karume, Ibrahim; Musa, Musa M.; Bsharat, Odey; Takahashi, Masateru; Hamdan, Samir M.; El Ali, Bassam; RSC Advances; vol. 6; nb. 99; (2016); p. 96616 - 96622 View in Reaxys

Li H

Rx-ID: 33825505 View in Reaxys 12/80 Yield

Conditions & References With triisopropoxytitanium(IV) chloride, (Sa)-2'-((S)-hydroxy(phenyl)methyl)-[1,1'-binaphthalen]-2-ol in diethyl ether, hexane, Time= 0.166667h, T= -20 °C , enantioselective reaction Veguillas, Marcos; Solà, Ricard; Shaw, Luke; Maciá, Beatriz; European Journal of Organic Chemistry; vol. 2016; nb. 9; (2016); p. 1788 - 1794 View in Reaxys Stage 1: With (Sa)-2'-[(R)-hydroxy(phenyl)methyl]-(1,1'-binaphthalen)-2-ol, titanium(IV)isopropoxide in toluene, Time= 1h, T= -40 °C , Inert atmosphere Stage 2: With hydrogenchloride in water, Inert atmosphere, optical yield given as percent ee, enantioselective reaction Fernandez-Mateos, Emilio; MacIa, Beatriz; Yus, Miguel; European Journal of Organic Chemistry; nb. 20; (2012); p. 3732 3736 View in Reaxys

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Li H O

Rx-ID: 42164488 View in Reaxys 13/80 Yield

Conditions & References With triisopropoxytitanium(IV) chloride, (Ra)-2'-[(S)-hydroxy(pyridin-4-yl)methyl]-(1,1'-binaphthalen)-2-ol in diethyl ether, hexane, Time= 0.166667h, T= -20 °C , enantioselective reaction Veguillas, Marcos; Solà, Ricard; Shaw, Luke; Maciá, Beatriz; European Journal of Organic Chemistry; vol. 2016; nb. 9; (2016); p. 1788 - 1794 View in Reaxys

O HO

(v4)

O H

Rx-ID: 42849729 View in Reaxys 14/80 Yield

Conditions & References 11 : 4.2. General procedure for the addition of methyltriisopropoxititanium to aldehydes-general procedure A General procedure: To a stirred solution of L1 or L2 (0.2 equiv) in Et2O (3.0mL, 0.067M) at 0°C, MeTi(OiPr)3 (0.3mL, 1.5equiv, 1M in THF, unless stated otherwise) was added. The solution was stirred for 1 min and then the aldehyde (0.1 mmol) was added. The reaction was stirred for 90 min and then quenched with water. The layers were separated and the aqueous layer was extracted three times with Et2O. The combined organic layers were dried over anhydrous MgSO4 and the solvent was removed under reduced pressure. The reaction crude was purified by flash silica gel chromatography. 4.2.11 (R)-1-Phenylpropan-2-ol 2k 21

Following general procedure A, the reaction of phenylacetaldehyde (12 μL, 0.1 mmol) with methyltriisopropoxytitanium (0.15 mL, 1.5 equiv, 1.0 M in THF) in the presence of (Ra,S)-Py-BINMOL L2 (3.8 mg, 0.1 equiv) in Et2O (1.5 mL) provided (R)-1phenylpropan-2-ol (13 mg) as a colorless oil after column chromatography (Hex/EtOAc 9:1). Yield: 93percent. Ee: 85percent. [β]D 25 = -35.4 (c 0.7, CHCl3) {Lit. 21

[β]D 28 = -35.4 (c 0.8, CHCl3) for 99percent ee}. Ee determination by chiral GC analysis, Cyclosil β column, T = 85 °C, P = 15.9 psi, retention times: tr(S) = 76.0 min, tr(R) = 78.2 min (major enantiomer). With (Ra)-2'-[(S)-hydroxy(pyridin-4-yl)methyl]-(1,1'-binaphthalen)-2-ol in tetrahydrofuran, diethyl ether, Time= 1h, T= 0 °C , Reagent/catalyst, Overall yield = 93 percent; Overall yield = 13 mg; enantioselective reaction Veguillas, Marcos; Solà, Ricard; Fernández-Ibañez, M. Ángeles; Maciá, Beatriz; Tetrahedron Asymmetry; vol. 27; nb. 14-15; (2016); p. 643 - 648 View in Reaxys

Rx-ID: 43934168 View in Reaxys 15/80

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Yield

Conditions & References With Candida antarctica lipase B, Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110A mutant, nicotinamide adenine dinucleotide phosphate, NADPH in hexane, Time= 24h, T= 50 °C , Resolution of racemate, enantioselective reaction Karume, Ibrahim; Musa, Musa M.; Bsharat, Odey; Takahashi, Masateru; Hamdan, Samir M.; El Ali, Bassam; RSC Advances; vol. 6; nb. 99; (2016); p. 96616 - 96622 View in Reaxys

Rx-ID: 44024819 View in Reaxys 16/80 Yield

Conditions & References With water, sodium hydroxide in methanol, Time= 6h Cozett, Rudy E.; Venter, Gerhard A.; Gokada, Maheswara Rao; Hunter, Roger; Organic and Biomolecular Chemistry; vol. 14; nb. 46; (2016); p. 10914 - 10925 View in Reaxys

Rx-ID: 26054982 View in Reaxys 17/80 Yield

Conditions & References With Candida antarctica lipase B immobilized on acrylic resin in tetrahydrofuran, hexane, T= 25 °C , p= 750.075Torr , Title compound not separated from byproducts. Csajagi, Csaba; Szatzker, Gabor; Rita Toke, Eniko; Uerge, Laszlo; Darvas, Ferenc; Poppe, Laszlo; Tetrahedron Asymmetry; vol. 19; nb. 2; (2008); p. 237 - 246 View in Reaxys With Candida antarctica lipase B in acetonitrile, Time= 18h, T= 30 °C , Resolution of racemate, Enzymatic reaction, stereoselective reaction Kitamoto, Yuichi; Kuruma, Yosuke; Suzuki, Kazumi; Hattori, Tetsutaro; Journal of Organic Chemistry; vol. 80; nb. 1; (2015); p. 521 - 527 View in Reaxys

HO Br

H HO

Rx-ID: 39553797 View in Reaxys 18/80 Yield

Conditions & References With [2,2]bipyridinyl, manganese, (1,2-dimethoxyethane)dichloronickel(II), bis(.eta.5((1R,2S,5R)-5-methyl-2-[prop-2-yl]-cyclohex-1-yl)cyclopentadienyl)-titanium dichloride, sodium thiophenolate, triethylamine hydrochloride in benzene, Time= 4h, T= 20 °C , Inert atmosphere, Glovebox, Autoclave, enantioselective reaction

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Zhao, Yang; Weix, Daniel J.; Journal of the American Chemical Society; vol. 137; nb. 9; (2015); p. 3327 - 3340 View in Reaxys

Rx-ID: 39553818 View in Reaxys 19/80 Yield 11 %

Conditions & References With [2,2]bipyridinyl, manganese, (1,2-dimethoxyethane)dichloronickel(II), bis(.eta.5((1R,2S,5R)-5-methyl-2-[prop-2-yl]-cyclohex-1-yl)cyclopentadienyl)-titanium dichloride, triethylamine hydrochloride in benzene, Time= 12h, T= 20 °C , Inert atmosphere, Glovebox, Autoclave, enantioselective reaction Zhao, Yang; Weix, Daniel J.; Journal of the American Chemical Society; vol. 137; nb. 9; (2015); p. 3327 - 3340 View in Reaxys

O H

H HO

Rx-ID: 39553819 View in Reaxys 20/80 Yield

Conditions & References With [2,2]bipyridinyl, manganese, (1,2-dimethoxyethane)dichloronickel(II), bis(.eta.5((1R,2S,5R)-5-methyl-2-[prop-2-yl]-cyclohex-1-yl)cyclopentadienyl)-titanium dichloride, sodium thiophenolate, triethylamine hydrochloride, Time= 2.5h, T= 20 °C , Inert atmosphere, Glovebox, Autoclave, enantioselective reaction Zhao, Yang; Weix, Daniel J.; Journal of the American Chemical Society; vol. 137; nb. 9; (2015); p. 3327 - 3340 View in Reaxys

HO O H

H HO

Rx-ID: 39553820 View in Reaxys 21/80 Yield

Conditions & References With [2,2]bipyridinyl, manganese, (1,2-dimethoxyethane)dichloronickel(II), bis(.eta.5((1R,2S,5R)-5-methyl-2-[prop-2-yl]-cyclohex-1-yl)cyclopentadienyl)-titanium dichloride, triethylamine hydrochloride in benzene, Time= 12h, T= 20 °C , Inert atmosphere, Glovebox, Autoclave, enantioselective reaction Zhao, Yang; Weix, Daniel J.; Journal of the American Chemical Society; vol. 137; nb. 9; (2015); p. 3327 - 3340 View in Reaxys

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Rx-ID: 41497327 View in Reaxys 22/80 Yield

Conditions & References With sodium perborate tetrahydrate in tetrahydrofuran, water, Inert atmosphere, Schlenk technique Borràs, Carlota; Biosca, Maria; Pàmies, Oscar; Diéguez, Montserrat; Organometallics; vol. 34; nb. 21; (2015); p. 5321 5334 View in Reaxys

Rx-ID: 41583797 View in Reaxys 23/80 Yield

Conditions & References With esterase from archaeon Sulfolobus tokodaii strain 7 in aq. buffer, Time= 2h, T= 30 °C , pH= 8, Resolution of racemate, Enzymatic reaction Wada, Reina; Ozaki, Masanaru; Kumon, Takashi; Ohta, Hiromichi; Miyamoto, Kenji; Biocatalysis and Biotransformation; vol. 33; nb. 3; (2015); p. 188 - 190 View in Reaxys

Rx-ID: 2152967 View in Reaxys 24/80 Yield

Conditions & References With sodium hydroxide, Time= 4h, T= 25 °C Bianchi, Daniele; Cesti, Pietro; Battistel, Ezio; Journal of Organic Chemistry; vol. 53; nb. 23; (1988); p. 5531 - 5534 View in Reaxys With lithium hydroxide in methanol, Time= 3h, T= 20 °C Shi, Xiao-Xin; Yao, Jian-Zhong; Kang, Li; Shen, Chun-Li; Yi, Fei; Journal of Chemical Research; nb. 10; (2004); p. 681 683 View in Reaxys With sodium hydroxide in methanol, water Kiss, Violetta; Egri, Gabriella; Balint, Jozsef; Ling, Istvan; Barkoczi, Jozsef; Fogassy, Elemer; Tetrahedron Asymmetry; vol. 17; nb. 15; (2006); p. 2220 - 2234 View in Reaxys With potassium hydroxide in tetrahydrofuran, methanol, Time= 12h Cordova; Tremblay; Clapham; Janda; Journal of Organic Chemistry; vol. 66; nb. 16; (2001); p. 5645 - 5648 View in Reaxys With water, potassium hydoxide in methanol Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910

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View in Reaxys

HO O

Rx-ID: 36507068 View in Reaxys 25/80 Yield

Conditions & References Stage 1: With magnesium in tetrahydrofuran, Time= 1h, T= 0 °C , Inert atmosphere Stage 2: With copper(l) cyanide in tetrahydrofuran, Time= 0.5h, T= -35 °C Stage 3: in tetrahydrofuran, Time= 1.5h, T= -35 - 20 °C Taguri, Tomonori; Yamamoto, Masanobu; Fujii, Toru; Muraki, Yuta; Ando, Tetsu; European Journal of Organic Chemistry; nb. 30; (2013); p. 6924 - 6933 View in Reaxys With pyridine, 1,3 -dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, 4,4'-bipyridine, NiI2*3.9H2O, triethylamine hydrochloride, sodium iodide, zinc, Time= 12h, T= 20 °C Zhao, Yang; Weix, Daniel J.; Journal of the American Chemical Society; vol. 136; nb. 1; (2014); p. 48 - 51 View in Reaxys

Rx-ID: 37560876 View in Reaxys 26/80 Yield

Conditions & References With D-Glucose in aq. phosphate buffer, dimethyl sulfoxide, Time= 4h, T= 30 °C , pH= 8, enantioselective reaction Yang, Yi; Liu, Ji; Li, Zhi; Angewandte Chemie - International Edition; vol. 53; nb. 12; (2014); p. 3120 - 3124; Angew. Chem.; vol. 126; nb. 12; (2014); p. 3348,1 View in Reaxys

HO H

Rx-ID: 37560878 View in Reaxys 27/80 Yield

Conditions & References With D-Glucose in aq. phosphate buffer, dimethyl sulfoxide, Time= 4h, T= 30 °C , pH= 8, Reagent/catalyst, enantioselective reaction Yang, Yi; Liu, Ji; Li, Zhi; Angewandte Chemie - International Edition; vol. 53; nb. 12; (2014); p. 3120 - 3124; Angew. Chem.; vol. 126; nb. 12; (2014); p. 3348,1 View in Reaxys

HO O

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O H

Rx-ID: 37926123 View in Reaxys 28/80 Yield

Conditions & References 2.6 General procedure for LH-EP immobilized SmL catalyzed resolution of racemic alcohols General procedure: A certain molar ratios of racemic alcohol and acyl donor such as vinyl butyrate in an organic solvent (5mL) was mixed with appropriate amount of immobilized lipase in a 25mL screw capped vial in a thermostatted shaker. The reaction was monitored and the ee assessed by HPLC analysis on the chiral columns as stated in the HPLC Analysis section. Aliquots (50μL) of the reaction mixture were withdrawn at intervals, diluted with n-hexane/2-propanol (9:1, 450μL), centrifuged and the supernatant (10μL) was then injected onto the column. With LH-EP immobilized Serratia marcescens H30 lipase in hexane, Time= 36h, T= 45 °C , Resolution of racemate, enantioselective reaction Su, Erzheng; Xu, Jingjing; You, Pengyong; Journal of Molecular Catalysis B: Enzymatic; vol. 106; (2014); p. 11 - 16 View in Reaxys

H HO

Rx-ID: 39376770 View in Reaxys 29/80 Yield

Conditions & References With D-glucose, GDH, cytochrome P450 monooxygenase CYP116B4 from Labrenzia aggregata, nicotinamide adenine dinucleotide phosphate in aq. buffer, Time= 5h, T= 30 °C , pH= 8.5, Enzymatic reaction, enantioselective reaction Yin, Yue-Cai; Yu, Hui-Lei; Luan, Zheng-Jiao; Li, Ren-Jie; Ouyang, Peng-Fei; Liu, Jing; Xu, Jian-He; ChemBioChem; vol. 15; nb. 16; (2014); p. 2443 - 2449 View in Reaxys With nicotinamide adenine dinucleotide phosphate, cytochrome P450 monooxygenase from Labrenzia aggregata in aq. buffer, Time= 5h, T= 30 °C , pH= 8.5, Enzymatic reaction, enantioselective reaction Yin, Yue-Cai; Yu, Hui-Lei; Luan, Zheng-Jiao; Li, Ren-Jie; Ouyang, Peng-Fei; Liu, Jing; Xu, Jian-He; ChemBioChem; vol. 15; nb. 16; (2014); p. 2443 - 2449 View in Reaxys

Rx-ID: 11097767 View in Reaxys 30/80 Yield

Conditions & References With [bis(acetoxy)iodo]benzene, potassium bromide in dichloromethane, water, Time= 1h, T= 20 °C Sun, Wei; Wu, Xiaomei; Xia, Chungu; Helvetica Chimica Acta; vol. 90; nb. 3; (2007); p. 623 - 626 View in Reaxys Stage 1: With C28H36ClMnN2O2, potassium acetate in dichloromethane, water, Time= 0.0833333h Stage 2: With N-Bromosuccinimide in dichloromethane, water, Time= 2h, T= 20 °C , Kinetics, enantioselective reaction

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Xu, Daqian; Wang, Shoufeng; Shen, Zhiqiang; Xia, Chungu; Sun, Wei; Organic and Biomolecular Chemistry; vol. 10; nb. 14; (2012); p. 2730 - 2732 View in Reaxys Typical procedure for the OKR of racemic secondary alcohols with C2-PhI(OAc)2 system General procedure: Typical procedure for the OKR of racemic secondary alcohols with C2-PhI(OAc)2 system To a 5 mL glass reactor substrate (0.25 mmol), catalyst C2 (0.005 mmol, 2 molpercent), CH2Cl2 (0.3 mL) and H2O (0.6 mL) were added and the resulting mass was magnetically stirred for 5 min. To the above stirring mass, KBr (4 molpercent) was added at room temperature. The reaction mixture was then cooled to 15 °C and PhI(OAc)2 (0.7 equiv.) was added slowly in small fractions over 15 min and stirring was continued to the specified time. After the completion of the reaction, catalyst was precipitated out by the addition of hexane to the reaction mixture. The recovered catalyst was dried and stored for future use. An aliquot of organic layer was subjected to HPLC analysis to determine enantiomeric excess (ee) of the product. The resulting ketone and enantio-enriched secondary alcohol were separated by silica gel flash chromatography. With [bis(acetoxy)iodo]benzene, C36H50ClMnN2O6, potassium bromide in dichloromethane, water, Time= 0.5h, T= 15 °C , Reagent/catalyst Bera, Prasanta Kumar; Maity, Nabin Ch.; Abdi, Sayed H.R.; Khan, Noor-Ul H.; Kureshy, Rukhsana I.; Bajaj, Hari C.; Applied Catalysis A: General; vol. 467; (2013); p. 542 - 551 View in Reaxys

Rx-ID: 36875236 View in Reaxys 31/80 Yield

Conditions & References With methanol, potassium carbonate, Time= 16h, Reflux, Inert atmosphere Kleman, Patryk; Gonzalez-Liste, Pedro J.; Garcia-Garrido, Sergio E.; Cadierno, Victorio; Pizzano, Antonio; Chemistry A European Journal; vol. 19; nb. 48; (2013); p. 16209 - 16212 View in Reaxys

Rx-ID: 36875272 View in Reaxys 32/80 Yield

Conditions & References Reaction Steps: 3 1: ruthenium / water / 24 h / 60 °C / Sealed tube; Inert atmosphere 2: C38H46O3P2*C7H8*Rh(1+)*BF4 (1-); hydrogen / dichloromethane / 24 h / 40 °C / 3000.3 Torr / Glovebox; Inert atmosphere 3: potassium carbonate; methanol / 16 h / Reflux; Inert atmosphere With methanol, C38H46O3P2*C7H8*Rh(1+)*BF4 (1-), hydrogen, potassium carbonate, ruthenium in dichloromethane, water Kleman, Patryk; Gonzalez-Liste, Pedro J.; Garcia-Garrido, Sergio E.; Cadierno, Victorio; Pizzano, Antonio; Chemistry A European Journal; vol. 19; nb. 48; (2013); p. 16209 - 16212 View in Reaxys

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O H

Rx-ID: 36875321 View in Reaxys 33/80 Yield

Conditions & References Reaction Steps: 2 1: C38H46O3P2*C7H8*Rh(1+)*BF4 (1-); hydrogen / dichloromethane / 24 h / 40 °C / 3000.3 Torr / Glovebox; Inert atmosphere 2: potassium carbonate; methanol / 16 h / Reflux; Inert atmosphere With methanol, C38H46O3P2*C7H8*Rh(1+)*BF4 (1-), hydrogen, potassium carbonate in dichloromethane Kleman, Patryk; Gonzalez-Liste, Pedro J.; Garcia-Garrido, Sergio E.; Cadierno, Victorio; Pizzano, Antonio; Chemistry A European Journal; vol. 19; nb. 48; (2013); p. 16209 - 16212 View in Reaxys

O B

Rx-ID: 33496904 View in Reaxys 34/80 Yield

Conditions & References With dihydrogen peroxide, sodium hydroxide in tetrahydrofuran, Time= 0.333333h, T= 0 °C , Cooling with ice Yi, Jun; Liu, Jin-Hui; Liang, Jun; Dai, Jian-Jun; Yang, Chu-Ting; Fu, Yao; Liu, Lei; Advanced Synthesis and Catalysis; vol. 354; nb. 9; (2012); p. 1685 - 1691 View in Reaxys

Al H

Rx-ID: 33714582 View in Reaxys 35/80 Yield

Conditions & References 4.2. General procedure for the synthesis of chiral alcohols General procedure: In a flame dried Schlenk tube, (Sa,R)-L1 (11.4 mg, 0.03 mmol) was dissolved in anhydrous Et2O (2.5 mL) and Ti(i-PrO)4 (366 μL, 4 equiv, 1.2 mmol) was added to the solution at 0 °C. After 5 min, R3Al (1.5 equiv, 0.45 mmol) was added followed by the addition of the corresponding aldehyde (0.3 mmol). The reaction mixture was stirred at 0 °C for 1 h (in the case of Me3Al) or 3 h (for the rest of organoaluminum reagents) and then quenched with 2 mL of H2O and 2 mL of HCl 2 M. The crude product was extracted with EtOAc (3 .x. 5 mL) and the combined organic layers were neutralized with aq satd NaHCO3, dried over MgSO4, and concentrated in vacuo. The crude product was purified by distillation or chromatography on silica gel to give the desired alcohol 2, whose data were in agreement with those previously reported in the literature.6c Stage 1: With titanium(IV) isopropylate, (Sa)-2'-[(R)-hydroxy(phenyl)methyl]-(1,1'-binaphthalen)-2-ol in diethyl ether, toluene, Time= 1h, T= 0 °C , Inert atmosphere Stage 2: With hydrogenchloride in diethyl ether, water, toluene, Inert atmosphere, optical yield given as percent ee, enantioselective reaction Fernandez-Mateos, Emilio; MacIa, Beatriz; Yus, Miguel; Tetrahedron Asymmetry; vol. 23; nb. 10; (2012); p. 789 - 794 View in Reaxys

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O O OH O

O O

HO O

Rx-ID: 34605496 View in Reaxys 36/80 Yield

Conditions & References With lipase from candida antartica in aq. phosphate buffer, Time= 48h, T= 30 °C Kataoka, Noriyuki; Okudomi, Masayuki; Chihara, Naoka; Matsumoto, Kazutsugu; Letters in Organic Chemistry; vol. 9; nb. 9; (2012); p. 615 - 621 View in Reaxys

O HO

O H

Rx-ID: 34605498 View in Reaxys 37/80 Yield

O O

O HO

Rx-ID: 34605539 View in Reaxys 38/80 Yield

Conditions & References Reaction Steps: 2 1: dmap / dichloromethane / 20 °C / Inert atmosphere 2: lipase from candida antartica / aq. phosphate buffer / 48 h / 30 °C

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With dmap, lipase from candida antartica in aq. phosphate buffer, dichloromethane Kataoka, Noriyuki; Okudomi, Masayuki; Chihara, Naoka; Matsumoto, Kazutsugu; Letters in Organic Chemistry; vol. 9; nb. 9; (2012); p. 615 - 621 View in Reaxys

O HO

O H

Rx-ID: 34605540 View in Reaxys 39/80 Yield

Conditions & References Reaction Steps: 2 1: dmap / dichloromethane / 20 °C / Inert atmosphere 2: lipase from candida antartica / aq. phosphate buffer / 48 h / 30 °C With dmap, lipase from candida antartica in aq. phosphate buffer, dichloromethane Kataoka, Noriyuki; Okudomi, Masayuki; Chihara, Naoka; Matsumoto, Kazutsugu; Letters in Organic Chemistry; vol. 9; nb. 9; (2012); p. 615 - 621 View in Reaxys

HO Mg

Rx-ID: 32115466 View in Reaxys 40/80 Yield

Conditions & References Stage 1: With titanium(IV) isopropylate, (Sa)-2'-[(R)-hydroxy(phenyl)methyl]-(1,1'-binaphthalen)-2-ol in toluene, Time= 0.166667h, T= -20 °C , Inert atmosphere Stage 2: in toluene, Time= 4h, T= -40 °C , Inert atmosphere, Grignard reaction, optical yield given as percent ee, enantioselective reaction Fernandez-Mateos, Emilio; MacIa, Beatriz; Ramon, Diego J.; Yus, Miguel; European Journal of Organic Chemistry; nb. 34; (2011); p. 6851 - 6855 View in Reaxys O

O OH

Rx-ID: 29753833 View in Reaxys 41/80 Yield

Conditions & References Stage 1: With dmap, dicyclohexyl-carbodiimide in dichloromethane, T= 20 °C , Inert atmosphere Stage 2: With immobilized Candida antarctica Lipase B, water in hexane, Time= 24h, T= 30 °C , pH= 6.5, aq. phosphate buffer, Enzymatic reaction Stage 3: With water, sodium hydroxide in methanol, Time= 1h, T= 20 °C , optical yield given as percent ee, enantioselective reaction

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Okudomi, Masayuki; Ageishi, Kanpei; Yamada, Tomomi; Chihara, Naoka; Nakagawa, Takuya; Mizuochi, Katsumi; Matsumoto, Kazutsugu; Tetrahedron; vol. 66; nb. 40; (2010); p. 8060 - 8067 View in Reaxys O

HO O OH

H O

Rx-ID: 29753834 View in Reaxys 42/80 Yield

Conditions & References Stage 1: With dmap, dicyclohexyl-carbodiimide in dichloromethane, T= 20 °C , Inert atmosphere Stage 2: With immobilized Candida antarctica Lipase B, water in hexane, Time= 24h, T= 30 °C , pH= 6.5, aq. phosphate buffer, Enzymatic reaction, optical yield given as percent ee, enantioselective reaction Okudomi, Masayuki; Ageishi, Kanpei; Yamada, Tomomi; Chihara, Naoka; Nakagawa, Takuya; Mizuochi, Katsumi; Matsumoto, Kazutsugu; Tetrahedron; vol. 66; nb. 40; (2010); p. 8060 - 8067 View in Reaxys

HO O

O H

Rx-ID: 29753836 View in Reaxys 43/80 Yield

Conditions & References Stage 1: With dmap, dicyclohexyl-carbodiimide in dichloromethane, T= 20 °C , Inert atmosphere Stage 2: With immobilized Candida antarctica Lipase B, water in hexane, Time= 24h, T= 30 °C , pH= 6.5, aq. phosphate buffer, Enzymatic reaction, optical yield given as percent ee, enantioselective reaction Okudomi, Masayuki; Ageishi, Kanpei; Yamada, Tomomi; Chihara, Naoka; Nakagawa, Takuya; Mizuochi, Katsumi; Matsumoto, Kazutsugu; Tetrahedron; vol. 66; nb. 40; (2010); p. 8060 - 8067 View in Reaxys

Cl H

Rx-ID: 29758101 View in Reaxys 44/80 Yield

Conditions & References With Pseudomonas fluorescence lipase, Resolution of racemate, Enzymatic reaction, optical yield given as percent ee Scholz, Roland; Hellmann, Gunther; Rohs, Susanne; Oezdemir, Diana; Raabe, Gerhard; Vermeeren, Cornelia; Gais, Hans-Joachim; European Journal of Organic Chemistry; nb. 24; (2010); p. 4588 - 4616 View in Reaxys

Rx-ID: 29809598 View in Reaxys 45/80

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Yield

Conditions & References With Sphingobium japonicum haloalkane dehalogenase, T= 21 °C , pH= 8.2, Tris sulfate buffer, Resolution of racemate, Enzymatic reaction, enantioselective reaction Prokop, Zbynek; Sato, Yukari; Brezovsky, Jan; Mozga, Tomas; Chaloupkova, Radka; Koudelakova, Tana; Jerabek, Petr; Stepankova, Veronika; Natsume, Ryo; Van Leeuwen, Jan G. E.; Janssen, Dick B.; Florian, Jan; Nagata, Yuji; Senda, Toshiya; Damborsky, Jiri; Angewandte Chemie - International Edition; vol. 49; nb. 35; (2010); p. 6111 - 6115 View in Reaxys

O Si O

Rx-ID: 31162024 View in Reaxys 46/80 Yield

Conditions & References With water, sodium hydroxide in tetrahydrofuran, methanol, T= 0 - 20 °C , Inert atmosphere, optical yield given as percent ee Addis, Daniele; Shaikh, Nadim; Zhou, Shaolin; Das, Shoubhik; Junge, Kathrin; Beller, Matthius; Chemistry - An Asian Journal; vol. 5; nb. 7; (2010); p. 1687 - 1691 View in Reaxys

Rx-ID: 28590413 View in Reaxys 47/80 Yield

Conditions & References With water in acetonitrile, Time= 24h, T= 25 °C , pH= 7, aq. phosphate buffer, optical yield given as percent ee Bonomi, Paolo; Cairoli, Paola; Ubiali, Daniela; Morelli, Carlo F.; Filice, Marco; Nieto, Ines; Pregnolato, Massimo; Manitto, Paolo; Terreni, Marco; Speranza, Giovanna; Tetrahedron Asymmetry; vol. 20; nb. 4; (2009); p. 467 - 472 View in Reaxys

Rx-ID: 28590414 View in Reaxys 48/80 Yield

Rx-ID: 2825781 View in Reaxys 49/80 Yield

Conditions & References With sodium hydroxide, Time= 4h, T= 25 °C

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Bianchi, Daniele; Cesti, Pietro; Battistel, Ezio; Journal of Organic Chemistry; vol. 53; nb. 23; (1988); p. 5531 - 5534 View in Reaxys With sodium hydroxide in methanol, water Kiss, Violetta; Egri, Gabriella; Balint, Jozsef; Ling, Istvan; Barkoczi, Jozsef; Fogassy, Elemer; Tetrahedron Asymmetry; vol. 17; nb. 15; (2006); p. 2220 - 2234 View in Reaxys

Rx-ID: 10305637 View in Reaxys 50/80 Yield

Conditions & References With sodium hydroxide in methanol, water Kiss, Violetta; Egri, Gabriella; Balint, Jozsef; Ling, Istvan; Barkoczi, Jozsef; Fogassy, Elemer; Tetrahedron Asymmetry; vol. 17; nb. 15; (2006); p. 2220 - 2234 View in Reaxys

HO O

O H

Rx-ID: 10504645 View in Reaxys 51/80 Yield

Conditions & References With polyoxyethylene (10) cetyl ether, n-octyl β-D-glucopyranoside, subtilisin Carlsberg, sodium carbonate in tetrahydrofuran, Time= 17h, T= 20 °C , Title compound not separated from byproducts Boren, Linnea; Martin-Matute, Belen; Xu, Yongmei; Cordova, Armando; Baeckvall, Jan-E.; Chemistry - A European Journal; vol. 12; nb. 1; (2006); p. 225 - 232 View in Reaxys

Rx-ID: 10025556 View in Reaxys 52/80 Yield

Conditions & References With Candida antarctica lipase B, chlorodicarbonyl(1,2,3,4,5-pentaphenylcyclopentadienyl)ruthenium(II), potassium tert-butylate, sodium carbonate in tetrahydrofuran, toluene, Time= 6h, T= 20 °C , Title compound not separated from byproducts Martin-Matute, Belen; Edin, Michaela; Bogar, Krisztian; Kaynak, F. Betuel; Baeckvall, Jan-E.; Journal of the American Chemical Society; vol. 127; nb. 24; (2005); p. 8817 - 8825

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View in Reaxys

H H HO

Rx-ID: 9717265 View in Reaxys 53/80 Yield

Conditions & References Stage 1: With (S)-2-methyl-quinazolinap rhodium, benzo[1,3,2]dioxaborole in tetrahydrofuran, Time= 2h, T= 0 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in tetrahydrofuran, ethanol, T= 0 - 20 °C , Title compound not separated from byproducts Connolly, David J.; Lacey, Patrick M.; McCarthy, Mary; Saunders, Cormac P.; Carroll, Anne-Marie; Goddard, Richard; Guiry, Patrick J.; Journal of Organic Chemistry; vol. 69; nb. 20; (2004); p. 6572 - 6589 View in Reaxys Stage 1: With (R)-2-tert-butyl-quinazolinap rhodium, benzo[1,3,2]dioxaborole in tetrahydrofuran, Time= 4h, T= 0 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in tetrahydrofuran, ethanol, T= 0 - 20 °C , Title compound not separated from byproducts Connolly, David J.; Lacey, Patrick M.; McCarthy, Mary; Saunders, Cormac P.; Carroll, Anne-Marie; Goddard, Richard; Guiry, Patrick J.; Journal of Organic Chemistry; vol. 69; nb. 20; (2004); p. 6572 - 6589 View in Reaxys

H H HO

Rx-ID: 9721780 View in Reaxys 54/80 Yield

Conditions & References Stage 1: With (R)-2-tert-butyl-quinazolinap rhodium, benzo[1,3,2]dioxaborole in tetrahydrofuran, Time= 2h, T= 20 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in tetrahydrofuran, ethanol, T= 0 - 20 °C , Title compound not separated from byproducts Connolly, David J.; Lacey, Patrick M.; McCarthy, Mary; Saunders, Cormac P.; Carroll, Anne-Marie; Goddard, Richard; Guiry, Patrick J.; Journal of Organic Chemistry; vol. 69; nb. 20; (2004); p. 6572 - 6589 View in Reaxys

Rx-ID: 9809798 View in Reaxys 55/80 Yield

Conditions & References Stage 1: With vinyl acetate, immobilized Novozym 435(R) Candida antarctica lipase-B in hexane, Time= 72h, T= 32 °C Stage 2: With triphenylstannane, 1,1'-azobis(1-cyanocyclohexanenitrile) in hexane, toluene, Time= 4h, Heating, Title compound not separated from byproducts Costa, Carlos E.; Clososki, Giuliano C.; Barchesi, Henrique B.; Zanotto, Sandra P.; Nascimento, M. Graca; Comasseto, Joao V.; Tetrahedron Asymmetry; vol. 15; nb. 24; (2004); p. 3945 - 3954

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View in Reaxys

Rx-ID: 9822582 View in Reaxys 56/80 Yield

Conditions & References With triphenylstannane, 1,1'-azobis(1-cyanocyclohexanenitrile) in toluene, Time= 4h, Heating Costa, Carlos E.; Clososki, Giuliano C.; Barchesi, Henrique B.; Zanotto, Sandra P.; Nascimento, M. Graca; Comasseto, Joao V.; Tetrahedron Asymmetry; vol. 15; nb. 24; (2004); p. 3945 - 3954 View in Reaxys

H HO

S O

Rx-ID: 13208402 View in Reaxys 57/80 Yield

Conditions & References Reaction Steps: 2 1: triethylamine / 3 h / 75 - 80 °C 2: aq. LiOH / methanol / 3 h / 20 °C With lithium hydroxide, triethylamine in methanol Shi, Xiao-Xin; Yao, Jian-Zhong; Kang, Li; Shen, Chun-Li; Yi, Fei; Journal of Chemical Research; nb. 10; (2004); p. 681 683 View in Reaxys

Rx-ID: 2070658 View in Reaxys 58/80 Yield

Conditions & References With water, Time= 168h, T= 30 °C , asymmetric hydrolysis and resolution by Pseudomonas cepacia, Product distribution Horiuchi, Kenichi; Kobashi, Kazunori; Nagata, Hidetomo; Satoh, Toshinobu; Suemitsu, Rikisaku; Bioscience, Biotechnology, and Biochemistry; vol. 58; nb. 7; (1994); p. 1330 - 1331 View in Reaxys With recombinant pig liver esterase in phosphate buffer, Time= 2h, pH= 7.5, Enzymatic reaction Musidlowska, Anna; Lange, Stefan; Bornscheuer, Uwe T.; Angewandte Chemie - International Edition; vol. 40; nb. 15; (2001); p. 2851 - 2853 View in Reaxys

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M g

Rx-ID: 15086972 View in Reaxys 59/80 Yield

Conditions & References Reaction Steps: 2 1.1: n-BuLi / tetrahydrofuran / 0.5 h / -30 °C 1.2: 68 percent / tetrahydrofuran / 1 h / 20 °C 2.1: Sphingomonas paucimobilis NCIMB 8195 / dimethylformamide; H2O; various solvent(s) / 120 h With n-butyllithium, Sphingomonas paucimobilis NCIMB 8195 in tetrahydrofuran, water, N,N-dimethyl-formamide Allan; Carnell; Journal of Organic Chemistry; vol. 66; nb. 19; (2001); p. 6495 - 6497 View in Reaxys

H Cl

Rx-ID: 5152223 View in Reaxys 60/80 Yield

Conditions & References With 4 A molecular sieve, chiral diamine, triethylamine in dichloromethane, Time= 3h, T= -78 °C , Yield given, Yields of byproduct given Sano, Tomohumi; Imai, Keisuke; Ohashi, Kousaburo; Oriyama, Takeshi; Chemistry Letters; nb. 3; (1999); p. 265 - 266 View in Reaxys

Rx-ID: 2204416 View in Reaxys 61/80 Yield

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Rx-ID: 3962198 View in Reaxys 62/80 Yield

Conditions & References Time= 24h, Lactobacillus kefir, Yield given Besse; Renard; Veschambre; Tetrahedron Asymmetry; vol. 5; nb. 7; (1994); p. 1249 - 1268 View in Reaxys

Rx-ID: 24393895 View in Reaxys 63/80 Yield

Conditions & References B : (R)-(-)-3-Phenyl-propan-2-ol STR106 (R)-(-)-3-Phenyl-propan-2-ol STR106 64 mg (76percent) of the title compound were obtained analogously as a colorless liquid of 44percent ee from 180 mg (0.62 mmol) of the carbamate from Example 7 of the formula I'. RF =0.33 (ether/pentane 1:1), [β]365 23 =-32.3 (c=1.90, ether). Example 6 of the formula I: Patent; Bayer Aktiengesellschaft; US5223633; (1993); (A) English View in Reaxys

Rx-ID: 2070659 View in Reaxys 64/80 Yield

Conditions & References With phosphate buffer, lipase, T= 20 °C Laumen, Kurt; Schneider, Manfred P.; Journal of the Chemical Society, Chemical Communications; (1988); p. 598 - 600 View in Reaxys With sodium hydroxide, dm-3 phosphate buffer, T= 25 °C , lipoprotein lipase from Pseudomonas aeruginosa (LPL Amano 1), pH 6.9-7.0 Kim, Mahn-Joo; Cho, Hangjin; Journal of the Chemical Society, Chemical Communications; nb. 19; (1992); p. 1411 - 1413 View in Reaxys

Rx-ID: 2505182 View in Reaxys 65/80 Yield

Conditions & References With nickel in tetrahydrofuran, Time= 2h, Ambient temperature Conte, V.; Furia, F. Di; Licini, G.; Modena, G.; Sbampato, G.; Valle, G.; Tetrahedron: Asymmetry; vol. 2; nb. 4; (1991); p. 257 - 276

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View in Reaxys

S O

Rx-ID: 21658223 View in Reaxys 66/80 Yield

Conditions & References Reaction Steps: 2 1: 56 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature 2: Raney-nickel / tetrahydrofuran / 2 h / Ambient temperature With tetrabutyl ammonium fluoride, nickel in tetrahydrofuran Conte, V.; Furia, F. Di; Licini, G.; Modena, G.; Sbampato, G.; Valle, G.; Tetrahedron: Asymmetry; vol. 2; nb. 4; (1991); p. 257 - 276 View in Reaxys

HO S

H S

Rx-ID: 2499347 View in Reaxys 67/80 Yield

Conditions & References With ethanol, nickel, T= 50 °C , or nBu3SnH, AIBN, toluene, reflux DeNinno; Perner; Lijewski; Tetrahedron Letters; vol. 31; nb. 51; (1990); p. 7415 - 7418 View in Reaxys O

HO S

H S

Rx-ID: 21672496 View in Reaxys 68/80 Yield

Conditions & References Reaction Steps: 2 1: borane / Corey catalyst / 0.5 h / Ambient temperature 2: 80 percent / EtOH / Raney nickel / 50 °C / or nBu3SnH, AIBN, toluene, reflux With ethanol, borane, nickel, pyridinium chlorochromate DeNinno; Perner; Lijewski; Tetrahedron Letters; vol. 31; nb. 51; (1990); p. 7415 - 7418 View in Reaxys

Rx-ID: 1983184 View in Reaxys 69/80 Yield

Conditions & References Yield given. Yields of byproduct given. Title compound not separated from byproducts

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Bianchi, Daniele; Cesti, Pietro; Battistel, Ezio; Journal of Organic Chemistry; vol. 53; nb. 23; (1988); p. 5531 - 5534 View in Reaxys

Cl H

Rx-ID: 4024756 View in Reaxys 70/80 Yield

Conditions & References With phosphate buffer, lipase, T= 20 °C Laumen, Kurt; Schneider, Manfred P.; Journal of the Chemical Society, Chemical Communications; (1988); p. 598 - 600 View in Reaxys

SiH O

Rx-ID: 3198430 View in Reaxys 71/80 Yield

Conditions & References With hydrogen cation in water, Yield given Brunner, Henri; Reiter, Barbara; Riepl, Georg; Chemische Berichte; vol. 117; nb. 4; (1984); p. 1330 - 1354 View in Reaxys

<2.4-dioxy-phenyl>-benzyl ketone

Rx-ID: 19999153 View in Reaxys 72/80 Yield

Conditions & References Reaction Steps: 2 1: <Rh(cycloocta-1,5-diene)Cl>2 / (S)-β-methyl-N-(phenyl-2-pyridinylmethylene)-phenylmethanamine (Rh:ligand = 1:9) / 46 h / 0 - 25 °C / var. of N-chelate ligands, Rh:ligand-proportion 2: H+ / H2O With hydrogen cation, chloro(1,5-cyclooctadiene)rhodium(I) dimer, (S)-1-phenyl-N-[(pyridin-2-yl)methylene]ethanamine in water Brunner, Henri; Reiter, Barbara; Riepl, Georg; Chemische Berichte; vol. 117; nb. 4; (1984); p. 1330 - 1354 View in Reaxys

H HO

H 2N

Rx-ID: 2198132 View in Reaxys 73/80

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Yield

Conditions & References With sodium nitrite in perchloric acid, water, Product distribution, Mechanism Kirmse, Wolfgang; Guenther, Bernd-Rainer; Loosen, Karin; Chemische Berichte; vol. 113; nb. 6; (1980); p. 2140 - 2153 View in Reaxys

Rx-ID: 4308187 View in Reaxys 74/80 Yield

Conditions & References (i) PBr5, CHCl3, (ii) Zn-Cu, aq. HCl, Multistep reaction Fischer,F.; Chemische Berichte; vol. 94; (1961); p. 893 - 901 View in Reaxys

O H

Rx-ID: 22765028 View in Reaxys 75/80 Yield

Conditions & References Reaction Steps: 2 1: aq. H2SO4 2: (i) PBr5, CHCl3, (ii) Zn-Cu, aq. HCl With sulfuric acid Fischer,F.; Chemische Berichte; vol. 94; (1961); p. 893 - 901 View in Reaxys

palladium/charcoal

Rx-ID: 5553930 View in Reaxys 76/80 Yield

Conditions & References Hydrogenation Witkop; Foltz; Journal of the American Chemical Society; vol. 79; (1957); p. 192,196 View in Reaxys

palladium/charcoal

Rx-ID: 5553931 View in Reaxys 77/80 Yield

Conditions & References Hydrogenation Witkop; Foltz; Journal of the American Chemical Society; vol. 79; (1957); p. 192,196

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View in Reaxys N O HO

Rx-ID: 1669 View in Reaxys 78/80 Yield

Conditions & References Kenyon; Phillips; Pittman; Journal of the Chemical Society; (1935); p. 1079 View in Reaxys

Br–

+Mg

(+)(R)-propylene oxide

Rx-ID: 8094921 View in Reaxys 79/80 Yield

Conditions & References With diethyl ether Levene; Walti; Journal of Biological Chemistry; vol. 90; (1931); p. 81,86 View in Reaxys

dl-methyl-benzyl-carbinol

Rx-ID: 8094922 View in Reaxys 80/80 Yield

Conditions & References ueber den sauren Phthalsaeureester und dessen Strychninsalz Pickard; Kenyon; Journal of the Chemical Society; vol. 105; (1914); p. 1124 View in Reaxys

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