Reaxys
PubChem
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Reactions (15)
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Substances (4)
Citations (36)
Conditions
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Rx-ID: 32641172 Find similar reactions
With (R)-N-methyl-1',2',3',4'-tetrahydro-1,1'-bisisoquinoline; copper(l) chloride in tetrahydrofuran
T=20°C; Henry reaction; 48 h; optical yield given as percent eeenantioselective reaction; Hide Experimental Procedure
Qiong Ji, Yao; Qi, Gao; Judeh, Zaher M.A.
Tetrahedron Asymmetry, 2011 , vol. 22, # 24 p. 2065 - 2070 Title/Abstract Full Text View citing articles Show Details
4.2. General procedure for the asymmetric Henry reaction
General procedure: At first, (R)-1b (0.02 mmol, 10 mol percent) and CuCl (0.02 mmol, 10 mol percent) were mixed in THF (1.5 mL) and allowed to stir at rt for 1 h. Aldehydes (0.2 mmol) and nitroethane/nitropropane (4 mmol, 20 equiv) were then added sequentially. The reaction mixture was then stirred at the given temperature for a specific time (TLC). The β-nitroalcohol product was purified on silica gel by flash column chromatography. With C17H12N3O2RhS; 1-ethyl-3-methylimidazolium tetrafluoroborate in ethanol
T=20°C; Henry Nitro Aldol Condensation; 8 h; Reagent/catalystConcentrationSolvent; Overall yield = 94 percent; Hide Experimental Procedure
Anitha; Manikandan; Vijayan; Anbuselvi; Viswanathamurthi
Journal of Organometallic Chemistry, 2015 , vol. 791, p. 244 - 251 Title/Abstract Full Text View citing articles Show Details
1:2.5 Catalysis
General procedure: A mixture of catalyst (3μmol) and ionic liquid (0.10mmol) in 2mL of ethanol was stirred for 15min. To this solution, nitroalkane (3mmol) and aldehyde (1mmol) were then added. The reaction mixture was stirred for 8hat room temperature and then the solvent was evaporated. The product was separated by repetitive washing of the residue with petroleum ether and ethyl acetate (8:2) mixture. After complete washing, the ionic liquid containing catalyst was dried under vacuum and stored in a desiccator for its use in subsequent catalytic runs. The product was then purified by column chromatography to afford the corresponding adduct as the product. The diastereoselectivity and enantiomeric excess of the products were determined by HPLC analysis. The 1H NMR data of the products were compared with the literature [43].
With (2R,5S)-5-isopropyl-2,5-dimethyl-2-(pyridine-2-yl)imidazolidine-4-thione; copper diacetate in isopropyl alcohol
T=6°C; Henry Nitro Aldol Condensation; 288 h; Overall yield = 72 percent; Overall yield = 86 percentSpectr.; enantioselective reaction;
Nováková, Gabriela; Drabina, Pavel; Frumarová, Božena; Sedlák, Miloš
Advanced Synthesis and Catalysis, 2016 , vol. 358, # 15 p. 2541 - 2552 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 10417331 Find similar reactions
With Hevea brasiliensis hydroxynitrile lyase in phosphate buffer
T=20°C; Henry reaction; pH=7; 48 h; Title compound not separated from byproducts;
Purkarthofer, Thomas; Gruber, Karl; Gruber-Khadjawi, Mandana; Waich, Kerstin; Skranc, Wolfgang; Mink, Daniel; Griengl, Herfried
Angewandte Chemie - International Edition, 2006 , vol. 45, # 21 p. 3454 - 3456 Title/Abstract Full Text View citing articles Show Details
With C17H26N2; copper(II) acetate monohydrate; N-ethyl-N,N-diisopropylamine in ethanol
T=-40°C; Henry reaction; optical yield given as percent eeenantioselective reaction;
Blay, Gonzalo; Domingo, Luis R.; Hernandez-Olmos, Victor; Pedro, Jose R.
Chemistry - A European Journal, 2008 , vol. 14, # 15 p. 4725 - 4730 Title/Abstract Full Text View citing articles Show Details
With C26H34BN2O2(1-)*H(1+); copper(II) bis(trifluoromethanesulfonate); triethylamine in ethanol T=20°C; Henry reaction; 24 h; Inert atmosphere; optical yield given as percent eestereoselective reaction;
Toussaint, Aurelie; Pfaltz, Andreas
European Journal of Organic Chemistry, 2008 , # 27 p. 4591 - 4597 Title/Abstract Full Text View citing articles Show Details
With 9-mercapto-epi-quinine; copper(II) acetate monohydrate in isopropyl alcohol
T=-20°C; Henry reaction; 72 h; optical yield given as percent eediastereoselective reaction;
Zielinska-Blajet, Mariola; Skarzewski, Jacek
Tetrahedron Asymmetry, 2009 , vol. 20, # 17 p. 1992 - 1998 Title/Abstract Full Text View citing articles Show Details
With brucin-OL; zinc trifluoromethanesulfonate; triethylamine in tetrahydrofuran; water
T=-15°C; Henry reaction; 24 h; Inert atmosphere; optical yield given as percent eeenantioselective reaction;
Kim, Hun Young; Oh, Kyungsoo
Organic Letters, 2009 , vol. 11, # 24 p. 5682 - 5685 Title/Abstract Full Text View citing articles Show Details
Stage #1: benzaldehyde With copper(II) acetate monohydrate; (1R,2R)-N,N'-di(anthracenyl-9'-methylene)-1,2-diaminocyclohexane in isopropyl alcohol
T=-30 - 23°C; Henry reaction; 0.25 h; Stage #2: Nitroethane With N-ethyl-N,N-diisopropylamine in isopropyl alcohol
T=-30°C; Henry reaction; 70 h; optical yield given as percent ee;
Kowalczyk, Rafal; Skarzewski, Jacek
Tetrahedron Asymmetry, 2009 , vol. 20, # 21 p. 2467 - 2473 Title/Abstract Full Text View citing articles Show Details
With C39H23F12N3 in tetrahydrofuran
T=-80°C; Henry reaction; Inert atmosphere; optical yield given as percent eeenantioselective reaction;
Ube, Hitoshi; Terada, Masahiro
Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 14 p. 3895 - 3898 Title/Abstract Full Text View citing articles Show Details
With copper(II) acetate monohydrate; triethylamine; (5aS,10aS)-(-)-Octahydro-5H,10H-dipyrrololt;1,2-a:1',2'-dgt;pyrazin in ethanol
T=-40°C; Henry reaction; 96 h; optical yield given as percent eeenantioselective reaction;
Selvakumar, Sermadurai; Sivasankaran, Dhanasekaran; Singh, Vinod K.
Organic and Biomolecular Chemistry, 2009 , vol. 7, # 15 p. 3156 - 3162 Title/Abstract Full Text View citing articles Show Details
With (-)-(1S,3R,4R)-2-[(S)-1-phenylethyl]-3-(benzylaminomethyl)-2-azabicyclo[2.2.1]heptane; copper(II) acetate monohydrate in isopropyl alcohol
T=0 - 20°C; Henry reaction; optical yield given as percent eeenantioselective reaction; Hide Experimental Procedure
Wojaczynska, Elbieta
Tetrahedron Asymmetry, 2011 , vol. 22, # 2 p. 161 - 166 Title/Abstract Full Text View citing articles Show Details
4.8. A general procedure for the nitroaldol reaction
General procedure: The ligand (0.06 mmol, 12 mol percent) and Cu(OAc)2*H2O (10.0 mg, 0.05 mmol, 10 mol percent) were dissolved in 1 mL of isopropanol and stirred for 1 h at room temperature. The appropriate aldehyde (0.5 mmol, 1 equiv) and nitroalkane (5.0 mmol, 10 equiv) were added with an additional 1 mL of i-PrOH. The reaction mixture was cooled to 0 °C. After 3 days, the crude product was isolated by column chromatography (n-hexane/AcOEt 6:1) to yield β-nitroalcohol or the desired β-nitroalcohols as a mixture of diastereomers. Products were analyzed by 1H NMR, and the enantiomeric excess was determined using chiral HPLC. With quinine-Cu(OAc)2 complex in isopropyl alcohol
T=0°C; Henry reaction; 72 h; optical yield given as percent eeenantioselective reaction; Hide Experimental Procedure
Zielinska-Blajet, Mariola; Skarzewski, Jacek
Tetrahedron Asymmetry, 2011 , vol. 22, # 3 p. 351 - 355 Title/Abstract Full Text View citing articles Show Details
4.2. General procedure for the nitroaldol reaction
General procedure: The ligand (0.06 mmol, 12 mol percent) and Cu(OAc)2*H2O (10.0 mg, 0.05 mmol, 10 mol percent) were dissolved in i-PrOH (1 mL) and the mixture was stirred for 3 h at rt to give a blue-green solution. The reaction mixture was cooled to 0 °C (or -20 °C). The respective aldehyde (0.5 mmol, 1 equiv) and nitroalkane (5.0 mmol, 10 equiv) were added with an additional 1 mL of i-PrOH. After 3 days, the crude product was isolated by column chromatography (hexane/AcOEt 6:1) to give β-nitroalcohol or desired β-nitroalcohols as a mixture of diastereomers. With CF3O3S(1-)*C19H24CuF3N4O3S(1+); triethylamine in methanol T=0°C; Henry reaction; Inert atmosphere;
Cooper, Christine J.; Jones, Matthew D.; Brayshaw, Simon K.; Sonnex, Benjamin; Russell, Mark L.; Mahon, Mary F.; Allan, David R.
Dalton Transactions, 2011 , vol. 40, # 14 p. 3677 - 3682 Title/Abstract Full Text View citing articles Show Details
Stage #1: Nitroethane With (3aR,3a'R,8aS,8a'S)-2,2'-[5-(anthracen-9-ylmethoxy)pentane-2,2-diyl]bis(8,8a-dihydro-3aH-indeno[1,2-d]oxazole); copper(II) acetate monohydrate in ethanol
T=20°C; Henry reaction; 0.166667 h; Inert atmosphere; Stage #2: benzaldehyde in ethanol
T=20°C; Henry reaction; 24 h; Inert atmosphere; enantioselective reaction;
Didier, Dorian; Magnier-Bouvier, Caroline; Schulz, Emmanuelle
Advanced Synthesis and Catalysis, 2011 , vol. 353, # 7 p. 1087 - 1095 Title/Abstract Full Text View citing articles Show Details
Stage #1: benzaldehyde With C56H58CuN4O4 in tetrahydrofuran
T=20°C; 1 h; Stage #2: Nitroethane With sodium carbonate in tetrahydrofuran
T=-20°C; asymmetric Henry reaction; 20 h; optical yield given as percent eediastereoselective reaction; Hide Experimental Procedure
Wei, Yu; Yao, Lin; Zhang, Bangle; He, Wei; Zhang, Shengyong
Tetrahedron, 2011 , vol. 67, # 44 p. 8552 - 8558 Title/Abstract Full Text View citing articles Show Details
4.3. General procedure for the asymmetric Henry reaction
General procedure: The metal/Schiff base catalyst (0.025 mmol) was dissolved in solvent (1 mL). Then, the corresponding aldehyde (0.25 mmol) was added. After stirring for 1 h at room temperature, the mixture was cool down to -20 °C (or to indicated temperature). Then nitroalkane (1.25 mmol) and the corresponding basic additive were added. The stirring was continued for indicated time and after that the reaction mixture was diluted with ether (3 mL). The resulting mixture suspension was filtered through a pad of Celite to remove the catalyst, and the filtrate solution was evaporated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (hexane/ether=9:1) to afford the product. With (R)-N-methyl-1',2',3',4'-tetrahydro-1,1'-bisisoquinoline; copper(l) chloride in di-isopropyl ether
T=20°C; Henry reaction; 48 h; optical yield given as percent eeenantioselective reaction;
Qiong Ji, Yao; Qi, Gao; Judeh, Zaher M.A.
Tetrahedron Asymmetry, 2011 , vol. 22, # 24 p. 2065 - 2070 Title/Abstract Full Text View citing articles Show Details
With (2R,5S)-5-(3,4-dimethoxybenzyl)-2,5-dimethyl-2-(pyridine-2-yl)imidazolidine-4-one; copper diacetate in ethanol
T=10°C; Henry Nitro Aldol Condensation; 288 h; Overall yield = 97 percentSpectr.; enantioselective reaction;
Drabina, Pavel; Karel, Sergej; Panov, Illia; Sedlak, Milos
Tetrahedron Asymmetry, 2013 , vol. 24, # 5-6 p. 334 - 339 Title/Abstract Full Text View citing articles Show Details
Stage #1: benzaldehyde With (1R,2R)-N1-(4-methylpentan-2-yl)cyclohexane-1,2-diamine; copper(II) acetate monohydrate in isopropyl alcohol
T=-40°C; Henry Nitro Aldol Condensation; 0.25 h; Stage #2: Nitroethane in isopropyl alcohol
Henry Nitro Aldol Condensation; 0.0833333 h; Stage #3: With triethylamine in isopropyl alcohol
T=-40°C; Henry Nitro Aldol Condensation; 24 h; Overall yield = 99percent; stereoselective reaction;
Liu, Fei; Gou, Shaohua; Li, Lei
Applied Organometallic Chemistry, 2014 , vol. 28, # 3 p. 186 - 193 Title/Abstract Full Text View citing articles Show Details
With 2-ethynylpyridine; (1R,2R)-N-benzyl-N'-(S)-binaphthyl-1,2-diphenylethandiamine; copper(II) acetate monohydrate in ethanol; dichloromethane
T=20°C; Henry Nitro Aldol Condensation; Inert atmosphere; Overall yield = 33 percent; diastereoselective reaction; Hide Experimental Procedure
Arai, Takayoshi; Joko, Akinori; Sato, Katsuya
Synlett, 2015 , vol. 26, # 2 art. no. ST-2014-U0755-L, p. 209 - 214 Title/Abstract Full Text View citing articles Show Details
Diastereoselective Henry Reaction To Give 2-Nitro-1-(2-nitrophenyl)propan-1-ol; General Procedure:
General procedure: The catalystwas prepared by complex formation between ligand L8 (6.4 mg,0.011 mmol) with Cu(OAc)2·H2O (2.0 mg, 0.01 mmol) in anhydrousCH2Cl2 (1.0 mL) under Ar. After stirring overnight at r.t.,the solvent was removed under reduced pressure and theresidue was dissolved in EtOH (0.4 mL). To the resulting clear,blue solution were added nitroethane (147 μL, 2 mmol), 2-ethynylpiridine (2.0 μL, 0.02 mmol), and the aldehyde (0.2mmol) under Ar. After stirring for the appropriate time, thereaction mixture was quenched with 1 M HCl and extractedwith CH2Cl2. The organic layer was washed with brine and thendried with sodium sulfate. After removal of the solvent underreduced pressure, the residue was purified by silica gel columnchromatography (n-hexane–EtOAc) to afford the adduct. Stage #1: benzaldehyde With CuOTf*(C7H8)0.5; C27H48N4O4 in tetrahydrofuran
T=35°C; Henry Nitro Aldol Condensation; 0.5 h; Molecular sieveInert atmosphere; Stage #2: Nitroethane With N-ethyl-N,N-diisopropylamine in tetrahydrofuran
T=-20°C; Henry Nitro Aldol Condensation; 72 h; Molecular sieveInert atmosphere; Overall yield = 99 percent; enantioselective reaction;
Mei, Hongjiang; Xiao, Xiao; Zhao, Xiaohu; Fang, Bing; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming
Journal of Organic Chemistry, 2015 , vol. 80, # 4 p. 2272 - 2280 Title/Abstract Full Text View citing articles Show Details
With (1R,2R)-N,N′-bis(furan-2-ylmethyl)cyclohexane-1,2-diamine; copper diacetate trihydrate in isopropyl alcohol
T=-30°C; Henry Nitro Aldol Condensation; 72 h; Overall yield = 73 percent; enantioselective reaction;
Cerisoli, Lucia; Grilli, Stefano; Savoia, Diego
Letters in Organic Chemistry, 2014 , vol. 11, # 9 p. 633 - 638 Title/Abstract Full Text View citing articles Show Details
With (1R,2R)-N,N'-bis-biphenyl-4-ylmethyl-cyclohexane-1,2-diamine; triethylamine; copper dichloride in ethyl acetate
T=0°C; Henry Nitro Aldol Condensation; 24 h; SolventReagent/catalyst; enantioselective reaction;
Tanaka, Koichi; Iwashita, Tomoharu; Yoshida, Erika; Ishikawa, Tomomi; Otuka, Shinya; Urbanczyk-Lipkowska, Zofia; Takahashi, Hiroki
Chemical Communications, 2015 , vol. 51, # 37 p. 7907 - 7910 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 32113373 Find similar reactions
Stage #1: benzaldehyde With 1,4-diaza-bicyclo[2.2.2]octane; C20H28N2; copper(II) acetate monohydrate in ethanol
T=0°C; Henry reaction; 0.25 h; Stage #2: Nitroethane in ethanol
T=0°C; Henry reaction; 24 h; optical yield given as percent eediastereoselective reaction;
Kodama, Koichi; Sugawara, Kazuyuki; Hirose, Takuji
Chemistry - A European Journal, 2011 , vol. 17, # 48 p. 13584 - 13592 Title/Abstract Full Text View citing articles Show Details
With copper(II) acetate monohydrate in tetrahydrofuran
T=27°C; Henry Nitro Aldol Condensation; 20 h; Overall yield = 88 percent; stereoselective reaction;
Das, Anjan; Choudhary, Manoj K.; Kureshy, Rukhsana I.; Roy, Tamal; Khan, Noor-Ul H.; Abdi, Sayed H.R.; Bajaj, Hari C.
ChemPlusChem, 2014 , vol. 79, # 8 p. 1138 - 1146 Title/Abstract Full Text View citing articles Show Details
Stage #1: benzaldehyde With CuOTf*(C7H8)0.5; C27H48N4O4 in tetrahydrofuran
T=35°C; Henry Nitro Aldol Condensation; 0.5 h; Molecular sieveInert atmosphere; Stage #2: Nitroethane With N-ethyl-N,N-diisopropylamine in tetrahydrofuran
T=-20°C; Henry Nitro Aldol Condensation; 72 h; Molecular sieveInert atmosphere; Overall yield = 99 percent; enantioselective reaction;
Mei, Hongjiang; Xiao, Xiao; Zhao, Xiaohu; Fang, Bing; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming
Journal of Organic Chemistry, 2015 , vol. 80, # 4 p. 2272 - 2280 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 37805575 Find similar reactions
With [Zn2(2-acetamidoterephthalate)2(4,4′-bipyridine)2-(H2O)(DMF)]n in methanol
T=70°C; Henry Nitro Aldol Condensation; 48 h; Kinetics; Reagent/catalystTimeConcentrationTemperatureSolvent; Overall yield = 95 percentSpectr.; Optical yield = 46 percent de;
Karmakar, Anirban; Guedes Da Silva, M. Fatima C.; Pombeiro, Armando J. L.
Dalton Transactions, 2014 , vol. 43, # 21 p. 7795 - 7810 Title/Abstract Full Text View citing articles Show Details
With copper(II) nitrate trihydrate in methanol
T=70°C; Henry Nitro Aldol Condensation; 24 h; Overall yield = 24 percent;
Karmakar, Anirban; Oliver, Clive L.; Roy, Somnath; Öhrström, Lars
Dalton Transactions, 2015 , vol. 44, # 22 p. 10156 - 10165 Title/Abstract Full Text View citing articles Show Details
With [Cu4((2S,2’S,2’’S)-2,2’,2’’-(benzenetricarbonyltris(azanediyl))tripropanoic acid(-2H))2(H2O)4(MeOH)4] in methanol
T=70°C; Henry Nitro Aldol Condensation; 10 h; SolventTemperatureTime; Overall yield = 78 percent;
Karmakar, Anirban; Oliver, Clive L.; Roy, Somnath; Öhrström, Lars
Dalton Transactions, 2015 , vol. 44, # 22 p. 10156 - 10165 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 40992771 Find similar reactions
With C13H24Cl2CuN2; triethylamine in tetrahydrofuran; nitromethane
T=-20°C; Henry Nitro Aldol Condensation; Overall yield = 90 percent; Optical yield = 72 percent de; enantioselective reaction;
Scharnagel, Dagmar; Müller, Andreas; Prause, Felix; Eck, Martin; Goller, Jessica; Milius, Wolfgang; Breuning, Matthias
Chemistry - A European Journal, 2015 , vol. 21, # 35 p. 12488 - 12500 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 29041469 Find similar reactions
With brucin-OL; copper (I) acetate in dichloromethane; tert-butyl alcohol
T=-15°C; Henry reaction; 30 h; Inert atmosphere; optical yield given as percent eeenantioselective reaction;
Kim, Hun Young; Oh, Kyungsoo
Organic Letters, 2009 , vol. 11, # 24 p. 5682 - 5685 Title/Abstract Full Text View citing articles Show Details
With C13H26N2; copper(II) acetate monohydrate; triethylamine in ethanol
T=-25°C; Henry reaction; 47 h; optical yield given as percent eeenantioselective reaction;
Noole, Artur; Lippur, Kristin; Metsala, Andrus; Lopp, Margus; Kanger, Tonis
Journal of Organic Chemistry, 2010 , vol. 75, # 4 p. 1313 - 1316 Title/Abstract Full Text View citing articles Show Details
With copper(II) choride dihydrate; C15H28N2; N-ethyl-N,N-diisopropylamine in tetrahydrofuran
T=-20°C; Henry reaction; 90 h; optical yield given as percent eeenantioselective reaction;
Zhou, Yirong; Dong, Junfang; Zhang, Fanglin; Gong, Yuefa
Journal of Organic Chemistry, 2011 , vol. 76, # 2 p. 588 - 600 Title/Abstract Full Text View citing articles Show Details
With 1-ethyl-piperidine; 3,5-bistrifluoromethylbenzoic acid; bis((3,5-bis(trifluoromethyl)phenyl)ureido)-(salen)cobalt in tert-butyl methyl ether
T=-70°C; Henry reaction; 48 h; optical yield given as percent eediastereoselective reaction;
Lang, Kai; Park, Jongwoo; Hong, Sukwon
Angewandte Chemie - International Edition, 2012 , vol. 51, # 7 p. 1620 - 1624 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 32789952 Find similar reactions
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Zhou, Zhi-Ming; Li, Zhi-Huai; Hao, Xiao-Yan; Zhang, Jun; Dong, Xiao; Liu, Ying-Qiang; Sun, Wen-Wen; Cao, Dan; Wang, JinLiang
Organic and Biomolecular Chemistry, 2012 , vol. 10, # 10 p. 2113 - 2118 Title/Abstract Full Text View citing articles Show Details
With 2C7H7O3S(1-)*C37H48N6O2(2+); copper (II) acetate monohydrate in methanol T=0°C; Henry reaction; 60 h; stereoselective reaction;
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Rx-ID: 34138466 Find similar reactions
Stage #1: 1-nitroethane With C36H46Cu2N2O4 in tert-butyl alcohol
T=20°C; Henry Nitro Aldol Condensation; 1.5 h; Stage #2: With 4-methoxy-phenol in tert-butyl alcohol
T=20°C; Henry Nitro Aldol Condensation; 1.5 h; Stage #3: 2-methyl-benzaldehyde in tert-butyl alcohol
T=20°C; Henry Nitro Aldol Condensation; 96 h; Overall yield = 82 percent; enantioselective reaction;
Boobalan, Ramalingam; Lee, Gene-Hsian; Chen, Chinpiao
Advanced Synthesis and Catalysis, 2012 , vol. 354, # 13 p. 2511 - 2520 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 30319247 Find similar reactions
With pyridine; C36H44N4O4S2; copper(I) bromide in methanol
Jin, Wei; Li, Xincheng; Wan, Boshun
Journal of Organic Chemistry, 2011 , vol. 76, # 2 p. 484 - 491 Title/Abstract Full Text View citing articles Show Details
T=20°C; Henry reaction; Inert atmosphere; optical yield given as percent eeenantioselective reaction;
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Multi-step reaction with 2 steps 1: (R)-N-methyl-1',2',3',4'-tetrahydro-1,1'-bisisoquinoline; copper(l) chloride / tetrahydrofuran 2: (R)-N-methyl-1',2',3',4'-tetrahydro-1,1'-bisisoquinoline; copper(l) chloride / di-isopropyl ether / 48 h / 20 °C View Scheme
Qiong Ji, Yao; Qi, Gao; Judeh, Zaher M.A.
Tetrahedron Asymmetry, 2011 , vol. 22, # 24 p. 2065 - 2070 Title/Abstract Full Text View citing articles Show Details
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Qiong Ji, Yao; Qi, Gao; Judeh, Zaher M.A.
Tetrahedron Asymmetry, 2011 , vol. 22, # 24 p. 2065 - 2070 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: (R)-N-methyl-1',2',3',4'-tetrahydro-1,1'-bisisoquinoline; copper(l) chloride / tetrahydrofuran 2: (R)-N-methyl-1',2',3',4'-tetrahydro-1,1'-bisisoquinoline; copper(l) chloride / tetrahydrofuran / 48 h / 20 °C View Scheme
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With C31H33CuF6N5O6S2; triethylamine in 1,4-dioxane
T=0°C; Henry reaction; 24 h; Inert atmosphere; optical yield given as percent eeenantioselective reaction;
Cheng, Liang; Dong, Jiaxing; You, Jingsong; Gao, Ge; Lan, Jingbo
Chemistry - A European Journal, 2010 , vol. 16, # 23 p. 6761 - 6765 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 29523827 Find similar reactions
B: 92%
With 4-methyl-morpholine; C31H33CuF6N5O6S2 in 1,4-dioxane
T=0°C; Henry reaction; 24 h; Inert atmosphere; optical yield given as percent eeenantioselective reaction;
Cheng, Liang; Dong, Jiaxing; You, Jingsong; Gao, Ge; Lan, Jingbo
Chemistry - A European Journal, 2010 , vol. 16, # 23 p. 6761 - 6765 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 28960195 Find similar reactions
Stage #1: 1-nitroethane With Yb(Oi-Pr)3; C18H20N2O4; water; sodium hexamethyldisilazane in tetrahydrofuran
T=0 - 20°C; Inert atmosphere; Stage #2: benzaldehyde in tetrahydrofuran
T=-40°C; 20 h; Inert atmosphere; optical yield given as percent ee;
Nitabaru, Tatsuya; Nojiri, Akihiro; Kobayashi, Makoto; Kumagai, Naoya; Shibasaki, Masakatsu
Journal of the American Chemical Society, 2009 , vol. 131, # 38 p. 13860 - 13869 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 11274192 Find similar reactions
B: 93%
Stage #1: PhCH(OH)CH2NO2 With potassium tert-butylate; chiral tetraaminophosphonium salt in tetrahydrofuran
T=-78°C; 0.5 h; Stage #2: benzaldehyde in tetrahydrofuran
T=-78°C; Henry reaction; 8 h; Further stages.;
Uraguchi, Daisuke; Sakaki, Sawako; Ooi, Takashi
Journal of the American Chemical Society, 2007 , vol. 129, # 41 p. 12392 - 12393 Title/Abstract Full Text View citing articles Show Details