(S)-2-Phenylcyclohexanone [C12H14O] by Asch

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51 reactions in Reaxys

2018-01-23 09h:10m:01s (EST)

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Rx-ID: 8613824 View in Reaxys 1/51 Yield

Conditions & References With cellulose tris(3,5-dichlorophenylcarbamate), enantioseparation of racemate Chankvetadze, Bezhan; Yamamoto, Chiyo; Okamoto, Yoshio; Chemistry Letters; nb. 4; (2000); p. 352 - 353 View in Reaxys With DCCD-HPS packed column, nickel(II) perchlorate in hydrogenchloride, acetonitrile, pH= 8.6 Gong, Yinhan; Lee, Hian Kee; Analytical Chemistry; vol. 75; nb. 6; (2003); p. 1348 - 1354 View in Reaxys Stage 1: With chloro-trimethyl-silane, triethylamine in N,N-dimethyl-formamide, Time= 90h, T= 130 °C , enolization; silylation Stage 2: With (R)-BINOL-SnCl4 in dichloromethane, toluene, Time= 1h, T= -78 °C , enantioselective protonation, Further stages. Title compound not separated from byproducts. Nakamura, Shingo; Kaneeda, Masanobu; Ishihara, Kazuaki; Yamamoto, Hisashi; Journal of the American Chemical Society; vol. 122; nb. 34; (2000); p. 8120 - 8130 View in Reaxys Stage 1: With t-Bu2SiCl, triethylamine in N,N-dimethyl-formamide, Time= 90h, T= 130 °C , enolization; silylation Stage 2: With (R)-BINOL-SnCl4 in dichloromethane, toluene, Time= 1h, T= -78 °C , enantioselective protonation, Further stages. Title compound not separated from byproducts. Nakamura, Shingo; Kaneeda, Masanobu; Ishihara, Kazuaki; Yamamoto, Hisashi; Journal of the American Chemical Society; vol. 122; nb. 34; (2000); p. 8120 - 8130 View in Reaxys Stage 1: With t-Bu2SiCl, triethylamine in N,N-dimethyl-formamide, Time= 90h, T= 130 °C , enolization; silylation Stage 2: With (S)-BINOL-SnCl4 in dichloromethane, toluene, Time= 1h, T= -78 °C , enantioselective protonation, Further stages. Title compound not separated from byproducts. Nakamura, Shingo; Kaneeda, Masanobu; Ishihara, Kazuaki; Yamamoto, Hisashi; Journal of the American Chemical Society; vol. 122; nb. 34; (2000); p. 8120 - 8130 View in Reaxys Resolution of racemate Ema, Tadashi; Tanida, Daisuke; Sugita, Kyoko; Sakai, Takashi; Miyazawa, Ken-Ichiro; Ohnishi, Atsushi; Organic Letters; vol. 10; nb. 12; (2008); p. 2365 - 2368 View in Reaxys 5; 4 :The separating agents prepared in Examples 1 and 2 were used as fillers, and filled in stainless columns each having a length of 25 cm and an inner diameter of 2 mm by a slurry filling method to make columns for enantiomeric isomers. Using those columns, optical resolution of enantiomeric compounds shown in Table 3 was performed by liquid chromatography. Analytical conditions are the mobile phase: hexane (H)/chloroform (C)/2-propanol (1) = 90/10/1, a flow rate: 0.1 or 0.2 ml/min, temperature: 25°C, and detection at 254 nm. The separation coefficient (α) in the table was determined by the following formula.Separation coefficient (α) = k2'/k1' : In the formula, k1' = ((t1-t0)/t0) and k2' = ( (t2-t0) /t0) . Those t1 and t2 denote elution times of respective enantiomeric isomers, and t0 denotes an elution time of tri-tert-butylbenzene. Table 1 shows the results when the mobile phase was hexane (H)/chloroform (C)/2-propanol (I) = 90/10/1.; Comparative Example 4 The optical resolution of various enantiomeric compounds was performed using the separating agents prepared in Comparative Examples 1 to 3 by the same method as that in Example 3. Table 1 shows the results. [Table 1] H/C/I=90/10/1 FillerEx. 1Ex. 2Com. Ex. 1Com. Ex. 2Com. Ex. 3Silica gelMA-SiM-SiA-SiMA-SiA-SiPolysaccharide derivative6-CMDMPC6-CMDMPC6-CMDMPC6-CVDMPC6CVDMPCAddition amount of styrene (percent)101010--Immobilization rate (percent)9080997050Enantiomeric compound 11.861.581.681.631.44Enantiomeric compound 21.601.951.01.41.62Enantiomeric compound 31.231.361.21.251.28Enantiomeric compound 41.211.231.21.151.16Enantiomeric compound

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51.371.311.361.31.28Enantiomeric compound 62.523.152.52.412.45Enantiomeric compound 71.01.01.01.01.0Enantiomeric compound 81.201.271.121.211.26Enantiomeric compound 92.042.241.81.911.56Mean of α values1.561.681.431.471.45 in hexane, chloroform, isopropyl alcohol, T= 25 °C , Resolution of racemate, Purification / work up Patent; Daicel Chemical Industries, Ltd.; EP1498404; (2005); (A1) English View in Reaxys 6 :The optical resolution of the enantiomeric compounds shown in Table 3 was performed by the same method as that in Example 5, except that the separating agents prepared in Examples 1 to 4 were used as fillers, the mobile phase was changed to hexane (H)/2-propanol = 90/10, and the flow rate was changed to 0.1 ml/min. Table 2 shows the results. in hexane, isopropyl alcohol, Resolution of racemate, Purification / work up Patent; Daicel Chemical Industries, Ltd.; EP1498404; (2005); (A1) English View in Reaxys 1.2.6 :In a nitrogen atmosphere, 20 ml of pyridine or dimethylsulfoxide was added to 1 g of a polysaccharide (cellulose or amylose), and each of the corresponding isocyanates (1) to (3) and (6) was added thereto in an amount of 1.5 equivalents to that of hydroxyl groups of the polysaccharide, and stirred under heating to thereby obtain each of polysaccharide benzoyl carbamate derivatives (7) to (13) shown in Table 1. In a nitrogen atmosphere, 20 ml of pyridine or dimethylsulfoxide was added to 1 g of a polysaccharide (cellulose or amylose), and each of the corresponding isocyanates (1) to (3) and (6) was added thereto in an amount of 1.5 equivalents to that of hydroxyl groups of the polysaccharide, and stirred under heating to thereby obtain each of polysaccharide benzoyl carbamate derivatives (7) to (13) shown in Table 1. (b) Surface Treatment of Silica GelPorous silica gel (particle size of 7 μm) was reacted with 3-aminopropyl triethoxysilane for aminopropylsilane (APS) treatment.(c) Preparation of Filler for Liquid Chromatography0.225 g of each of the polysaccharide benzoyl carbamate derivatives (7) to (13) obtained in the above section (a) was dissolved in tetrahydrofuran (THF) or dimethylsulfoxide (DMSO), and 0.9 g of silica gel obtained in the above section (b) was evenly coated with the resulting solution. Then, the solvent was distilled off under reduced pressure, to thereby obtain a filler for enantiomeric isomers having the target polysaccharide derivative carried on silica gel.(d) Preparation of Column for Liquid ChromatographyThe filler obtained in the above section (c) was pressed and filled into a stainless column of 0.2 cmΦ.x.25 cmL through a slurry filling method, to thereby prepare an enantiomeric isomer separation column. The enantiomeric isomer separation columns prepared in Examples were each evaluated for asymmetry identifying power (retention factor k' value and separation factor α value) by using the following ten compounds by means of liquid chromatography. Table 2 shows the results.(Analysis Conditions) Mobile phase: hexane/2-propanol=90/10 (v/v)Flow rate: 0.1 ml/minDetection: 254 nmTemperature: 25° C. With SiO2-supported amylose tris(3,5-dimethylbenzoyl)carbamate in hexane, isopropyl alcohol, T= 25 °C , Resolution of racemate, Product distribution / selectivity Patent; Daicel Chemical Industries, Ltd.; US7683167; (2010); (B2) English View in Reaxys 1-6 :The optical resolution of ten kinds of racemic bodies (FIG. 3) with the column-1 obtained by the above-mentioned operation (column temperature: about 20° C.) was performed. A HPLC pump (trade name: PU-980) manufactured by JASCO Corporation was used. The detection and identification of a peak were performed with a UV detector (wavelength: 254 nm, trade name: UV-970, manufactured by JASCO Corporation) and an optical rotation detector (trade name: OR-990, manufactured by JASCO Corporation) under the following conditions: a mixture of hexane and 2-propanol at a ratio of 95:5 was used as an eluent, and its flow rate was 0.2 ml/min. It should be noted that the number of theoretical plates N was determined from the peak of benzene, and a time to for which the eluent passed through the column was determined from the elution time of 1,3,5-tri-tert-butylbenzene.It should be noted that conditions concerning, for example, HPLC and a detector used in the evaluation for optical resolution identical to those described above were used in the following examples and comparative examples.Table 1 shows the results of the optical resolution with the column-1. Values in the table are a capacity ratio k1' and a separation factor α, and a sign in parentheses represents the optical activity of an enantiomer which was previously eluted.It should be noted that the capacity ratio k1' and the separation factor α are defined by the following formulae. A capacity ratio and a separation factor were calculated in the following examples and comparative examples by using the same formulae.Capacity ratio k1'k1'=[(retention time of enantiomer)-(t0)]/t0 [Num 1] Separation factor αα=(capacity ratio of enantiomer to be retained more strongly)/(capacity ratio of enantiomer to be retained more weakly) [Num 2]; [Table 1] TABLE 1 Optical resolutions of columns 1 to 4 Column-1a Column-2b Column-3a Column-4b Racemates k1' α k1' α k1' α k1' α 1 7.61(-) 1.30 5.97(-) 1.23 6.02(-) 1.23 4.30(-) 1.21 2 5.42(+) 1.58 5.13(+) 1.37 6.02(+) 1.09 3.69(+) 1.26 3 4.01(-)

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1.17 3.49(-) 1.76 3.34(-) 1.99 2.63(-) 1.74 4 11.49(+) 1.20 - 9.48(+) 1.19 5.63(+) 1.19 5 16.40(-) 3.90 7.96(-) 3.22 13.08(-) 2.80 5.38(-) 2.89 6 21.19(+) 1.26 13.59(+) 1.37 16.15(+) 1.43 9.08(+) 1.38 7 9.26(-) 1.13 7.44(-) 1.26 7.83(-) 1.29 5.57(-) 1.23 8 5.10(+) 1.26 2.35(+) 1.27 4.01(+) 1.27 - 9 20.00(-) 2.20 10.84(-) 2.50 24.13(-) 3.16 7.69(-) 2.57 10 20.75 1.00 6.63(+) 1.52 10.01(+) 1.91 4.12(+) 1.83 aEluent: hexane/2-propanol (95/5)bEluent: hexane/2-propanol (90/10) Column: 25 .x. 0.20 cm (i.d.), Flow rate: 0.2 ml/min With cellulose 3,5-dimethylphenylcarbamate in hexane, isopropyl alcohol, T= 20 °C , Resolution of racemate, Product distribution / selectivity Patent; Okamoto, Yoshio; Yamamoto, Chiyo; Ikai, Tomoyuki; Kamigaito, Masami; US2009/124798; (2009); (A1) English View in Reaxys 2-4 :The optical resolution of ten kinds of racemic bodies (FIG. 3) with the column-3 obtained by the above-mentioned operation were performed. The detection and identification of a peak were performed with a UV detector and an optical rotation detector under the following conditions: a mixture of hexane and 2-propanol at a ratio of 95:5 was used as an eluent, and its flow rate was 0.2 ml/min. It should be noted that the number of theoretical plates N was determined from the peak of benzene, and a time to for which the eluent passed through the column was determined from the elution time of 1,3,5-tri-tert-butylbenzene.Table 1 shows the results of the optical resolution with the column-3; [Table 1] TABLE 1 Optical resolutions of columns 1 to 4 Column-1a Column-2b Column-3a Column-4b Racemates k1' α k1' α k1' α k1' α 1 7.61(-) 1.30 5.97(-) 1.23 6.02(-) 1.23 4.30(-) 1.21 2 5.42(+) 1.58 5.13(+) 1.37 6.02(+) 1.09 3.69(+) 1.26 3 4.01(-) 1.17 3.49(-) 1.76 3.34(-) 1.99 2.63(-) 1.74 4 11.49(+) 1.20 - 9.48(+) 1.19 5.63(+) 1.19 5 16.40(-) 3.90 7.96(-) 3.22 13.08(-) 2.80 5.38(-) 2.89 6 21.19(+) 1.26 13.59(+) 1.37 16.15(+) 1.43 9.08(+) 1.38 7 9.26(-) 1.13 7.44(-) 1.26 7.83(-) 1.29 5.57(-) 1.23 8 5.10(+) 1.26 2.35(+) 1.27 4.01(+) 1.27 - 9 20.00(-) 2.20 10.84(-) 2.50 24.13(-) 3.16 7.69(-) 2.57 10 20.75 1.00 6.63(+) 1.52 10.01(+) 1.91 4.12(+) 1.83 aEluent: hexane/2-propanol (95/5)bEluent: hexane/2-propanol (90/10) Column: 25 .x. 0.20 cm (i.d.), Flow rate: 0.2 ml/min With cellulose 3,5-dimethylphenylcarbamate in hexane, isopropyl alcohol, Resolution of racemate, Product distribution / selectivity Patent; Okamoto, Yoshio; Yamamoto, Chiyo; Ikai, Tomoyuki; Kamigaito, Masami; US2009/124798; (2009); (A1) English View in Reaxys 2-5 :The optical resolution of nine kinds of racemic bodies (FIG. 3) with the column-2 obtained by the above-mentioned operation was performed. The detection and identification of a peak were performed with a UV detector and an optical rotation detector under the following conditions: a mixture of hexane and 2-propanol at a ratio of 90:10 was used as an eluent, and its flow rate was 0.2 ml/min. It should be noted that the number of theoretical plates N was determined from the peak of benzene, and a time to for which the eluent passed through the column was determined from the elution time of 1,3,5-tri-tert-butylbenzene.Table 1 shows the results of the optical resolution with the column-2. Values in the table are a capacity ratio k1' and a separation factor α, and a sign in parentheses represents the optical activity of an enantiomer which was previously eluted; [Table 1] TABLE 1 Optical resolutions of columns 1 to 4 Column-1a Column-2b Column-3a Column-4b Racemates k1' α k1' α k1' α k1' α 1 7.61(-) 1.30 5.97(-) 1.23 6.02(-) 1.23 4.30(-) 1.21 2 5.42(+) 1.58 5.13(+) 1.37 6.02(+) 1.09 3.69(+) 1.26 3 4.01(-) 1.17 3.49(-) 1.76 3.34(-) 1.99 2.63(-) 1.74 4 11.49(+) 1.20 - 9.48(+) 1.19 5.63(+) 1.19 5 16.40(-) 3.90 7.96(-) 3.22 13.08(-) 2.80 5.38(-) 2.89 6 21.19(+) 1.26 13.59(+) 1.37 16.15(+) 1.43 9.08(+) 1.38 7 9.26(-) 1.13 7.44(-) 1.26 7.83(-) 1.29 5.57(-) 1.23 8 5.10(+) 1.26 2.35(+) 1.27 4.01(+) 1.27 - 9 20.00(-) 2.20 10.84(-) 2.50 24.13(-) 3.16 7.69(-) 2.57 10 20.75 1.00 6.63(+) 1.52 10.01(+) 1.91 4.12(+) 1.83 aEluent: hexane/2-propanol (95/5)bEluent: hexane/2-propanol (90/10) Column: 25 .x. 0.20 cm (i.d.), Flow rate: 0.2 ml/min With cellulose 3,5-dimethylphenylcarbamate in hexane, isopropyl alcohol, Resolution of racemate, Product distribution / selectivity Patent; Okamoto, Yoshio; Yamamoto, Chiyo; Ikai, Tomoyuki; Kamigaito, Masami; US2009/124798; (2009); (A1) English View in Reaxys 3-4 :The optical resolution of nine kinds of racemic bodies (FIG. 3) with the column-4 obtained by the above-mentioned operation was performed. The detection and identification of a peak were performed with a UV detector and an optical rotation detector under the following conditions: a mixture of hexane and 2-propanol at a ratio of 90:10 was used as an eluent, and its flow rate was 0.1 ml/min. It should be noted that the number of theoretical plates N was determined from the peak of benzene, and a time to for which the eluent passed through the column was determined from the elution time of 1,3,5-tri-tert-butylbenzene. Table 1 shows the results of the optical resolution with the

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column-4.[Table 1] TABLE 1 Optical resolutions of columns 1 to 4 Column-1a Column-2b Column-3a Column-4b Racemates k1' α k1' α k1' α k1' α 1 7.61(-) 1.30 5.97(-) 1.23 6.02(-) 1.23 4.30(-) 1.21 2 5.42(+) 1.58 5.13(+) 1.37 6.02(+) 1.09 3.69(+) 1.26 3 4.01(-) 1.17 3.49(-) 1.76 3.34(-) 1.99 2.63(-) 1.74 4 11.49(+) 1.20 - 9.48(+) 1.19 5.63(+) 1.19 5 16.40(-) 3.90 7.96(-) 3.22 13.08(-) 2.80 5.38(-) 2.89 6 21.19(+) 1.26 13.59(+) 1.37 16.15(+) 1.43 9.08(+) 1.38 7 9.26(-) 1.13 7.44(-) 1.26 7.83(-) 1.29 5.57(-) 1.23 8 5.10(+) 1.26 2.35(+) 1.27 4.01(+) 1.27 - 9 20.00(-) 2.20 10.84(-) 2.50 24.13(-) 3.16 7.69(-) 2.57 10 20.75 1.00 6.63(+) 1.52 10.01(+) 1.91 4.12(+) 1.83 aEluent: hexane/2-propanol (95/5)bEluent: hexane/2-propanol (90/10) Column: 25 .x. 0.20 cm (i.d.), Flow rate: 0.2 ml/min With cellulose 3,5-dimethylphenylcarbamate in hexane, isopropyl alcohol, Resolution of racemate, Product distribution / selectivity Patent; Okamoto, Yoshio; Yamamoto, Chiyo; Ikai, Tomoyuki; Kamigaito, Masami; US2009/124798; (2009); (A1) English View in Reaxys 4 :Example 4[Production of Column for HPLC With CSP-2]CSP-2 (3.5 g) was dispersed in methanol, and then a stainless column having a diameter of 0.46 cm and a length of 25 cm was filled with the resultant slurry according to a slurry mode. Thus, a column filled with CSP-2 was produced.CSP-2 was evaluated for its asymmetry recognition ability with the resultant column under four kinds of evaluation conditions. The racemic bodies of Compounds 1 to 9 were used as samples for evaluation. The following evaluation of the chiral stationary phase for its asymmetry recognition ability is described for the respective evaluation conditions.[Evaluation (1)]The evaluation for the asymmetry recognition ability was performed with nine kinds of samples for evaluation (Compound Nos.: 1, 2, 3, 4, 5, 6, 7, 8, and 9) under the following conditions by HPLC. Table 5 shows the results of the evaluation. In addition, FIGS. 22 to 30 illustrate the chromatograms of the respective samples for evaluation. With CSP-2 column in hexane, isopropyl alcohol, T= 25 °C , Resolution of racemate, Product distribution / selectivity Patent; Ema, Tadashi; Sakai, Takashi; Tanida, Daisuke; Sugita, Kyoko; Ohnishi, Atsushi; Miyazawa, Kenichiro; US2010/292464; (2010); (A1) English View in Reaxys Reaction Steps: 2 1: pyridine; sodium iodide / hexane; acetonitrile / 20 h / 20 °C 2: (R)-N-(5,5,4,4,3,3,2,2-octafluoropentyl)-tert-butanesulfinamide; 2,6-di- tert-butylphenol; 2,4-dinitrobenzenesulfonic acid; sodium sulfate / toluene / -78 - -50 °C With pyridine, 2,6-di- tert-butylphenol, 2,4-dinitrobenzenesulfonic acid, (R)-N-(5,5,4,4,3,3,2,2-octafluoropentyl)-tertbutanesulfinamide, sodium sulfate, sodium iodide in hexane, toluene, acetonitrile Beck, Elizabeth M.; Hyde, Alan M.; Jacobsen, Eric N.; Organic Letters; vol. 13; nb. 16; (2011); p. 4260 - 4263 View in Reaxys Reaction Steps: 2 1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: silver tetrafluoroborate; (R)-BINAP(AuCl)2 / propan-1-ol; dichloromethane / 16 h / 20 °C / Inert atmosphere With silver tetrafluoroborate, n-butyllithium, (R)-BINAP(AuCl)2, diisopropylamine in tetrahydrofuran, propan-1-ol, hexane, dichloromethane Cheon, Cheol Hong; Kanno, Osamu; Toste, F. Dean; Journal of the American Chemical Society; vol. 133; nb. 34; (2011); p. 13248 - 13251 View in Reaxys With C49H76N4O4, 3-chloro-benzenecarboperoxoic acid, scandium tris(trifluoromethanesulfonate) in ethyl acetate, Time= 18h, T= -20 °C , Baeyer-Villiger Ketone Oxidation, Reagent/catalyst, Temperature, Time, enantioselective reaction Zhou, Lin; Liu, Xiaohua; Ji, Jie; Zhang, Yuheng; Hu, Xiaolei; Lin, Lili; Feng, Xiaoming; Journal of the American Chemical Society; vol. 134; nb. 41; (2012); p. 17023 - 17026,4 View in Reaxys With C49H76N4O4, 3-chloro-benzenecarboperoxoic acid, scandium tris(trifluoromethanesulfonate) in ethyl acetate, Time= 18h, T= -20 °C , Baeyer-Villiger Ketone Oxidation, enantioselective reaction

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Zhou, Lin; Liu, Xiaohua; Ji, Jie; Zhang, Yuheng; Hu, Xiaolei; Lin, Lili; Feng, Xiaoming; Journal of the American Chemical Society; vol. 134; nb. 41; (2012); p. 17023 - 17026 View in Reaxys With Xylan Phenylcarbamate Derivative coated on theaminopropylsilanized silica gel. Column: 25 cm x 0.20 cm ID in hexane, isopropyl alcohol, Resolution of racemate, Reagent/catalyst Li, Geng; Shen, Jun; Li, Qiang; Okamoto, Yoshio; Chirality; vol. 27; nb. 8; (2015); p. 518 - 522 View in Reaxys With chiral poly(phenylacetylene)polymer coated on aminopropyl silanized silica gel in hexane, isopropyl alcohol, Resolution of racemate, Reagent/catalyst Zhang, Chunhong; Ma, Rui; Wang, Hailun; Sakai, Ryosuke; Satoh, Toshifumi; Kakuchi, Toyoji; Liu, Lijia; Okamoto, Yoshio; Chirality; vol. 27; nb. 8; (2015); p. 500 - 506 View in Reaxys With cellulose derivative which bears a fullerene (C60) moiety at the 6-position-based chiral stationary phase in hexane, isopropyl alcohol, T= 25 °C , Resolution of racemate Gao, Bo; Xu, Zeyu; Fan, Luan; Xu, Xiaodong; Bai, Jianwei; Shen, Xiande; Chemistry Letters; vol. 44; nb. 11; (2015); p. 1479 - 1481 View in Reaxys With high-performance liquid chromatography column with poly[diphenylacetylene, (h-poly-(2S0.36-co-30.64))]-based chiral stationary phases in hexane, isopropyl alcohol, Resolution of racemate, enantioselective reaction Maeda, Katsuhiro; Maruta, Miyuki; Sakai, Yuki; Ikai, Tomoyuki; Kanoh, Shigeyoshi; Molecules; vol. 21; nb. 11; (2016); Art.No: 1487 View in Reaxys With 3‐aminopropyl silica gel treated with amylose 2‐benzoate‐3‐(3,5-dimethylphenylcarbamate)‐6‐(phenylcarbamate) in hexane, isopropyl alcohol, Resolution of racemate, Reagent/catalyst, Solvent Tang, Shouwan; Jin, Zhaolei; Sun, Baishen; Wang, Fang; Tang, Wenyuan; Chirality; vol. 29; nb. 9; (2017); p. 512 - 521 View in Reaxys

Rx-ID: 44341580 View in Reaxys 2/51 Yield

Conditions & References With 2-oxo-Δ3-4,5,5-trimethylcyclopentenylacetyl-coenzyme A monooxygenase from Pseudomonas putida NCIMB 10007, NADPH, Enzymatic reaction, Baeyer-Villiger Ketone Oxidation, enantioselective reaction Rudroff, Florian; Fink, Michael J.; Pydi, Ramana; Bornscheuer, Uwe T.; Mihovilovic, Marko D.; Monatshefte fur Chemie; vol. 148; nb. 1; (2017); p. 157 - 165 View in Reaxys

Rx-ID: 4075103 View in Reaxys 3/51 Yield

Conditions & References With (R)-binaphthol-SnCl4 in dichloromethane, Time= 0.0833333h, T= -100 °C , enantioselective protonation silyl enol ethers and ketene bis(trialkylsilyl) acetals; var. solv, temp.

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Ishihara, Kazuaki; Kaneeda, Masanobu; Yamamoto, Hisashi; Journal of the American Chemical Society; vol. 116; nb. 24; (1994); p. 11179 - 11180 View in Reaxys With (R,R)-2-phenyloctahydrobenzolt;1,3,2gt;diazaborole, multistep reaction, various chiral aminoboranes, Product distribution Yanagisawa, Akira; Inanami, Hiroshi; Yamamoto, Hisashi; Chemical Communications; nb. 15; (1998); p. 1573 1574 View in Reaxys With 2.6-dimethylphenol, tin(IV) chloride, (Ra)-1-(2-methoxynaphthalen-1-yl)naphthalen-2-ol in dichloromethane, toluene, Time= 0.0833333h, T= -80 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Ishihara; Nakamura; Kaneeda; Yamamoto; Journal of the American Chemical Society; vol. 118; nb. 50; (1996); p. 12854 - 12855 View in Reaxys With n-butyllithium, (R,R)-2-phenyloctahydrobenzolt;1,3,2gt;diazaborole, 1.) THF, hexane, 0 deg C, 2.) THF, hexane, toluene, -78 deg C, 2 h, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Yanagisawa, Akira; Inanami, Hiroshi; Yamamoto, Hisashi; Chemical Communications; nb. 15; (1998); p. 1573 1574 View in Reaxys With R-(-)-2-methoxy-2-phenyl ethanol, titanium tetrachloride in dichloromethane, Time= 1h, T= -78 °C , Product distribution, Further Variations: Reagents, Temperatures, time Nakashima, Daisuke; Yamamoto, Hisashi; Synlett; nb. 1; (2006); p. 150 - 152; Art.No: Y07805ST View in Reaxys With (S)-{3,3'-bis(4-t-butyl-2,6-diisopropylphenyl)-1,1'-binaphthalen-2,2'-yl}-N-triflyl-thiophosphoramide, phenol in toluene, Time= 8h, T= 20 °C , Inert atmosphere, Reactivity, Solvent, Reagent/catalyst, Time, Concentration, optical yield given as percent ee, enantioselective reaction Cheol, Hong Cheon; Yamamoto, Hisashi; Journal of the American Chemical Society; vol. 130; nb. 29; (2008); p. 9246 - 9247 View in Reaxys With methanol, (S)-2′-(diphenylphosphino)-1,1′-binaphthyl-2-ol, lanthanum(lll) triflate in dichloromethane, Time= 18h, T= 20 °C , Inert atmosphere, optical yield given as percent ee, enantioselective reaction Cheon, Cheol Hong; Imahori, Tatsushi; Yamamoto, Hisashi; Chemical Communications; vol. 46; nb. 37; (2010); p. 6980 - 6982 View in Reaxys With 2,6-di- tert-butylphenol, 2,4-dinitrobenzenesulfonic acid, (R)-N-(5,5,4,4,3,3,2,2-octafluoropentyl)-tert-butanesulfinamide, sodium sulfate in toluene, T= -78 - -50 °C , optical yield given as percent ee, enantioselective reaction Beck, Elizabeth M.; Hyde, Alan M.; Jacobsen, Eric N.; Organic Letters; vol. 13; nb. 16; (2011); p. 4260 - 4263 View in Reaxys With silver tetrafluoroborate, (R)-BINAP(AuCl)2 in propan-1-ol, dichloromethane, Time= 16h, T= 20 °C , Inert atmosphere, optical yield given as percent ee, enantioselective reaction Cheon, Cheol Hong; Kanno, Osamu; Toste, F. Dean; Journal of the American Chemical Society; vol. 133; nb. 34; (2011); p. 13248 - 13251 View in Reaxys With (R)-3,3′-dibromo vanol in toluene, Time= 2h, T= 20 °C , UV-irradiation, Solvent, Temperature, Overall yield = 64 percentSpectr.; enantioselective reaction Das, Anjan; Ayad, Suliman; Hanson, Kenneth; Organic Letters; vol. 18; nb. 20; (2016); p. 5416 - 5419 View in Reaxys

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Rx-ID: 28154864 View in Reaxys 4/51 Yield

Conditions & References With (S)-{3,3'-bis(2,4,6-triisopropylphenyl)-1,1'-binaphthalen-2,2'-yl}-N-triflyl-thiophosphoramide, acetic acid in toluene, Time= 12h, T= 20 °C , Inert atmosphere, optical yield given as percent ee, enantioselective reaction Cheol, Hong Cheon; Yamamoto, Hisashi; Journal of the American Chemical Society; vol. 130; nb. 29; (2008); p. 9246 - 9247 View in Reaxys With (R)-3,3′-dibromo vanol in toluene, Time= 2h, T= 20 °C , UV-irradiation, Overall yield = 78 percentSpectr.; enantioselective reaction Das, Anjan; Ayad, Suliman; Hanson, Kenneth; Organic Letters; vol. 18; nb. 20; (2016); p. 5416 - 5419 View in Reaxys

Rx-ID: 31549573 View in Reaxys 5/51 Yield

Conditions & References With C19H25F6N3O2S, 2,4-dinitrobenzenesulfonic acid in toluene, T= -78 - -40 °C , optical yield given as percent ee, enantioselective reaction Beck, Elizabeth M.; Hyde, Alan M.; Jacobsen, Eric N.; Organic Letters; vol. 13; nb. 16; (2011); p. 4260 - 4263 View in Reaxys With (R)-3,3′-dibromo vanol in toluene, Time= 2h, T= 20 °C , UV-irradiation, Overall yield = 64 percentSpectr.; enantioselective reaction Das, Anjan; Ayad, Suliman; Hanson, Kenneth; Organic Letters; vol. 18; nb. 20; (2016); p. 5416 - 5419 View in Reaxys

Rx-ID: 44507222 View in Reaxys 6/51 Yield

Conditions & References With (R)-3,3′-dibromo vanol in toluene, Time= 2h, T= 20 °C , UV-irradiation, Overall yield = 61 percent; Overall yield = 0.1 g; enantioselective reaction Das, Anjan; Ayad, Suliman; Hanson, Kenneth; Organic Letters; vol. 18; nb. 20; (2016); p. 5416 - 5419 View in Reaxys

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Rx-ID: 9392345 View in Reaxys 7/51 Yield 98 %

Conditions & References With Oxone, sodium ortho-iodobenzenesulfonate in acetonitrile, Time= 1h, T= 70 °C Uyanik, Muhammet; Akakura, Matsujiro; Ishihara, Kazuaki; Journal of the American Chemical Society; vol. 131; (2009); p. 251 - 262 View in Reaxys

98 %

With 5-F-AZADO+NO3-, acetic acid, Time= 2h, T= 20 °C Shibuya, Masatoshi; Osada, Yuji; Sasano, Yusuke; Tomizawa, Masaki; Iwabuchi, Yoshiharu; Journal of the American Chemical Society; vol. 133; nb. 17; (2011); p. 6497 - 6500 View in Reaxys

98 %

Stage 1: With copper(I) bromide in acetonitrile, Time= 0.05h, T= 20 °C , Inert atmosphere Stage 2: With N,N'-di-tert-butyldiaziridinone in acetonitrile, Time= 11h, T= 20 °C Zhu, Yingguang; Zhao, Baoguo; Shi, Yian; Organic Letters; vol. 15; nb. 5; (2013); p. 992 - 995 View in Reaxys

98 %

With 2-aza-6-oxaadamantane N-oxyl, sodium nitrite in acetic acid, Time= 6.5h, T= 20 °C , Reagent/catalyst, Time Shibuya, Masatoshi; Nagasawa, Shota; Osada, Yuji; Iwabuchi, Yoshiharu; Journal of Organic Chemistry; vol. 79; nb. 21; (2014); p. 10256 - 10268 View in Reaxys

93 %

With 1,3,5,7-tetrakis-(4-(diacetoxyiodo)phenyl)adamantane, 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl in dichloromethane, T= 20 °C Dohi, Toshifumi; Fukushima, Kei-Ichiro; Kamitanaka, Tohru; Morimoto, Koji; Takenaga, Naoko; Kita, Yasuyuki; Green Chemistry; vol. 14; nb. 5; (2012); p. 1493 - 1501 View in Reaxys

90 %

With 2-azaadamantane-N-oxyl, oxygen in aq. acetate buffer, Time= 12h, T= 20 °C , pH= 4.5, Green chemistry, Enzymatic reaction, Catalytic behavior, Reagent/catalyst, chemoselective reaction Zhu, Chenjie; Zhang, Zhi; Ding, Weiwei; Xie, Jingjing; Chen, Yong; Wu, Jinglan; Chen, Xiaochun; Ying, Hanjie; Green Chemistry; vol. 16; nb. 3; (2014); p. 1131 - 1138 View in Reaxys

84.3 %

With pyridinium chlorochromate in dichloromethane, Time= 15h, Inert atmosphere, Molecular sieve Leung, Diana; Anslyn, Eric V.; Organic Letters; vol. 13; nb. 9; (2011); p. 2298 - 2301 View in Reaxys

83 %

With tetraethylammonium bromide in water-d2, Time= 3h, T= 20 °C , optical yield given as percent ee Takenaga, Naoko; Goto, Akihiro; Yoshimura, Misaki; Fujioka, Hiromichi; Dohi, Toshifumi; Kita, Yasuyuki; Tetrahedron Letters; vol. 50; nb. 26; (2009); p. 3227 - 3229 View in Reaxys

75 %

With sodium dichromate in water, Time= 0.5h Kandula, SubbaRao V.; Puranik, Vedavati G.; Kumar, Pradeep; Tetrahedron Letters; vol. 44; nb. 27; (2003); p. 5015 - 5017 View in Reaxys With pyridinium chlorochromate in dichloromethane, T= 5 °C Bui; Hansen; Stenstrom; Hudlicky; Ribbons; New Journal of Chemistry; vol. 25; nb. 1; (2001); p. 116 - 124

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View in Reaxys 61 %Spectr.

With C10H16NO5, potassium carbonate, bis-[(trifluoroacetoxy)iodo]benzene, Time= 18h, T= 20 °C , Catalytic behavior, Reagent/catalyst Hamada, Shohei; Furuta, Takumi; Wada, Yoshiyuki; Kawabata, Takeo; Angewandte Chemie - International Edition; vol. 52; nb. 31; (2013); p. 8093 - 8097; Angew. Chem.; vol. 125; nb. 31; (2013); p. 8251 - 8255,5 View in Reaxys

OH racemate

Rx-ID: 28591272 View in Reaxys 8/51 Yield

Conditions & References

48 %, 52 %

With (1S,3R,4S,5R,7R)-N-hydroxy-4-benzyl-1-n-butyl-2-azaadamantane, sodium hydrogencarbonate in dichloromethane, Time= 3h, T= -40 °C , Resolution of racemate, Inert atmosphere, optical yield given as percent ee, enantioselective reaction Tomizawa, Masaki; Shibuya, Masatoshi; Iwabuchi, Yoshiharu; Organic Letters; vol. 11; nb. 8; (2009); p. 1828 1831 View in Reaxys

48 %, 52 %

With trichloroisocyanuric acid, (1R,3R,6R,7S,8R)-7-benzyl-3-n-butyl-4-oxa-5-azahomoadamantane, sodium hydrogencarbonate in dichloromethane, Time= 12h, T= -40 °C , Inert atmosphere, Reagent/catalyst, Temperature, enantioselective reaction Murakami, Keiichi; Sasano, Yusuke; Tomizawa, Masaki; Shibuya, Masatoshi; Kwon, Eunsang; Iwabuchi, Yoshiharu; Journal of the American Chemical Society; vol. 136; nb. 50; (2014); p. 17591 - 17600 View in Reaxys

OH racemate

Rx-ID: 39281268 View in Reaxys 9/51 Yield

Conditions & References With sodium hypochlorite, (1R,3R,6R,7S,8R)-7-benzyl-3-methyl-4-oxa-5-azahomoadamantane, sodium hydrogencarbonate in dichloromethane, Time= 0.5h, T= 0 °C , Inert atmosphere, Reagent/catalyst, Temperature, enantioselective reaction Murakami, Keiichi; Sasano, Yusuke; Tomizawa, Masaki; Shibuya, Masatoshi; Kwon, Eunsang; Iwabuchi, Yoshiharu; Journal of the American Chemical Society; vol. 136; nb. 50; (2014); p. 17591 - 17600 View in Reaxys

OH racemate

Rx-ID: 40165607 View in Reaxys 10/51 Yield 48 %

Conditions & References With trichloroisocyanuric acid, (1R,3S,6R,7S,8R)-7-benzyl-3-n-buthyl-4-oxa-5-azahomoadamantane, sodium hydrogencarbonate in dichloromethane, Time= 3h, T= -40 °C , Inert atmosphere Tomizawa, Masaki; Shibuya, Masatoshi; Iwabuchi, Yoshiharu; Organic Letters; vol. 16; nb. 18; (2014); p. 4968 4968

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View in Reaxys

Sn Br

Rx-ID: 35428764 View in Reaxys 11/51 Yield

Conditions & References

95 %

Stage 1: With (R)-2-(dicyclohexylphosphino)-2′-(2-naphthyloxy)-1,1'-binaphthyl, sodium acetate, palladium diacetate in diethyl ether, Time= 0.166667h, T= 25 °C , Glovebox, Inert atmosphere Stage 2: in diethyl ether, dodecane, Time= 26h, T= 25 °C , Glovebox, Inert atmosphere Huang, Zhiyan; Lim, Li Hui; Chen, Zuliang; Li, Yongxin; Zhou, Feng; Su, Haibin; Zhou, Jianrong; Angewandte Chemie - International Edition; vol. 52; nb. 18; (2013); p. 4906 - 4911; Angew. Chem.; (2013); p. 5006 - 5011,6 View in Reaxys

O Cl

Rx-ID: 35428773 View in Reaxys 12/51 Yield

Conditions & References Stage 1: With (R)-2-(dicyclohexylphosphino)-2′-(2-naphthyloxy)-1,1'-binaphthyl, sodium acetate, palladium diacetate in diethyl ether, Time= 0.166667h, T= 25 °C , Glovebox, Inert atmosphere Stage 2: in diethyl ether, dodecane, Time= 48h, T= 50 °C , Glovebox, Inert atmosphere, Overall yield = 93 percent; Overall yield = 78 mg Huang, Zhiyan; Lim, Li Hui; Chen, Zuliang; Li, Yongxin; Zhou, Feng; Su, Haibin; Zhou, Jianrong; Angewandte Chemie - International Edition; vol. 52; nb. 18; (2013); p. 4906 - 4911; Angew. Chem.; (2013); p. 5006 - 5011,6 View in Reaxys

F F

S O

O O

Rx-ID: 35428804 View in Reaxys 13/51 Yield

Conditions & References

96 %

Stage 1: With (R)-N-isopropyl-2-(dicyclohexylphosphino)-2'-(3-aminophenoxy)-1,1'-binaphthyl, sodium acetate, palladium diacetate in diethyl ether, Time= 0.166667h, T= 25 °C , Glovebox, Inert atmosphere Stage 2: in diethyl ether, dodecane, Time= 6h, T= 25 °C , Glovebox, Inert atmosphere Huang, Zhiyan; Lim, Li Hui; Chen, Zuliang; Li, Yongxin; Zhou, Feng; Su, Haibin; Zhou, Jianrong; Angewandte Chemie - International Edition; vol. 52; nb. 18; (2013); p. 4906 - 4911; Angew. Chem.; (2013); p. 5006 - 5011,6 View in Reaxys

O O O

Rx-ID: 34269829 View in Reaxys 14/51

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Yield

Conditions & References

46 %

With C49H76N4O4, aluminum isopropoxide, 3-chloro-benzenecarboperoxoic acid, scandium tris(trifluoromethanesulfonate) in ethyl acetate, Time= 36h, T= -40 °C , Baeyer-Villiger Ketone Oxidation, Reagent/catalyst, Temperature, Time, enantioselective reaction Zhou, Lin; Liu, Xiaohua; Ji, Jie; Zhang, Yuheng; Hu, Xiaolei; Lin, Lili; Feng, Xiaoming; Journal of the American Chemical Society; vol. 134; nb. 41; (2012); p. 17023 - 17026,4 View in Reaxys

46 %

With C49H76N4O4, aluminum isopropoxide, 3-chloro-benzenecarboperoxoic acid, scandium tris(trifluoromethanesulfonate) in ethyl acetate, Time= 36h, T= -40 °C , Baeyer-Villiger Ketone Oxidation, enantioselective reaction Zhou, Lin; Liu, Xiaohua; Ji, Jie; Zhang, Yuheng; Hu, Xiaolei; Lin, Lili; Feng, Xiaoming; Journal of the American Chemical Society; vol. 134; nb. 41; (2012); p. 17023 - 17026 View in Reaxys

46 %

With C49H76N4O4, aluminum isopropoxide, 3-chloro-benzenecarboperoxoic acid, scandium tris(trifluoromethanesulfonate) in ethyl acetate, Time= 36h, T= -40 °C , Baeyer-Villiger Ketone Oxidation, enantioselective reaction Zhou, Lin; Liu, Xiaohua; Ji, Jie; Zhang, Yuheng; Hu, Xiaolei; Lin, Lili; Feng, Xiaoming; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 20208 - 20208 View in Reaxys

O O O

Rx-ID: 34568088 View in Reaxys 15/51 Yield

Conditions & References With C49H76N4O4, 3-chloro-benzenecarboperoxoic acid, scandium tris(trifluoromethanesulfonate) in ethyl acetate, Time= 24h, T= 0 °C , Baeyer-Villiger Ketone Oxidation, Reagent/catalyst, enantioselective reaction Zhou, Lin; Liu, Xiaohua; Ji, Jie; Zhang, Yuheng; Hu, Xiaolei; Lin, Lili; Feng, Xiaoming; Journal of the American Chemical Society; vol. 134; nb. 41; (2012); p. 17023 - 17026 View in Reaxys With C49H76N4O4, aluminum isopropoxide, 3-chloro-benzenecarboperoxoic acid, scandium tris(trifluoromethanesulfonate) in ethyl acetate, Time= 24h, T= 0 °C , Baeyer-Villiger Ketone Oxidation, Reagent/catalyst, enantioselective reaction Zhou, Lin; Liu, Xiaohua; Ji, Jie; Zhang, Yuheng; Hu, Xiaolei; Lin, Lili; Feng, Xiaoming; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 20208 - 20208 View in Reaxys

Rx-ID: 34568089 View in Reaxys 16/51 Yield 51 %

Conditions & References With scandium isopropoxide, C49H76N4O4, 3-chloro-benzenecarboperoxoic acid, scandium tris(trifluoromethanesulfonate) in ethyl acetate, Time= 24h, T= 0 °C , Baeyer-Villiger Ketone Oxidation, enantioselective reaction Zhou, Lin; Liu, Xiaohua; Ji, Jie; Zhang, Yuheng; Hu, Xiaolei; Lin, Lili; Feng, Xiaoming; Journal of the American Chemical Society; vol. 134; nb. 41; (2012); p. 17023 - 17026 View in Reaxys

51 %

With scandium isopropoxide, C49H76N4O4, 3-chloro-benzenecarboperoxoic acid, scandium tris(trifluoromethanesulfonate) in ethyl acetate, Time= 24h, T= -10 °C , Baeyer-Villiger Ketone Oxidation, enantioselective reaction

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Zhou, Lin; Liu, Xiaohua; Ji, Jie; Zhang, Yuheng; Hu, Xiaolei; Lin, Lili; Feng, Xiaoming; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 20208 - 20208 View in Reaxys

O O

Rx-ID: 34568090 View in Reaxys 17/51 Yield

Conditions & References

38 %

With C49H76N4O4, aluminum isopropoxide, 3-chloro-benzenecarboperoxoic acid, scandium tris(trifluoromethanesulfonate) in ethyl acetate, Time= 24h, T= 0 °C , Baeyer-Villiger Ketone Oxidation, enantioselective reaction Zhou, Lin; Liu, Xiaohua; Ji, Jie; Zhang, Yuheng; Hu, Xiaolei; Lin, Lili; Feng, Xiaoming; Journal of the American Chemical Society; vol. 134; nb. 41; (2012); p. 17023 - 17026 View in Reaxys With C49H76N4O4, aluminum isopropoxide, 3-chloro-benzenecarboperoxoic acid, scandium tris(trifluoromethanesulfonate) in ethyl acetate, Time= 24h, T= 0 °C , Baeyer-Villiger Ketone Oxidation, enantioselective reaction Zhou, Lin; Liu, Xiaohua; Ji, Jie; Zhang, Yuheng; Hu, Xiaolei; Lin, Lili; Feng, Xiaoming; Journal of the American Chemical Society; vol. 134; nb. 49; (2012); p. 20208 - 20208 View in Reaxys

Rx-ID: 31549574 View in Reaxys 18/51 Yield

Rx-ID: 31549585 View in Reaxys 19/51 Yield

Conditions & References Reaction Steps: 3 1: tris-(dibenzylideneacetone)dipalladium(0); tributyltin fluoride; triethylamine; tri tert-butylphosphoniumtetrafluoroborate / benzene / 24 h / 80 °C / Inert atmosphere 2: pyridine; sodium iodide / hexane; acetonitrile / 20 h / 20 °C 3: (R)-N-(5,5,4,4,3,3,2,2-octafluoropentyl)-tert-butanesulfinamide; 2,6-di- tert-butylphenol; 2,4-dinitrobenzenesulfonic acid; sodium sulfate / toluene / -78 - -50 °C With pyridine, tris-(dibenzylideneacetone)dipalladium(0), 2,6-di- tert-butylphenol, 2,4-dinitrobenzenesulfonic acid, (R)N-(5,5,4,4,3,3,2,2-octafluoropentyl)-tert-butanesulfinamide, tributyltin fluoride, sodium sulfate, triethylamine, sodium iodide, tri tert-butylphosphoniumtetrafluoroborate in hexane, toluene, acetonitrile, benzene Beck, Elizabeth M.; Hyde, Alan M.; Jacobsen, Eric N.; Organic Letters; vol. 13; nb. 16; (2011); p. 4260 - 4263 View in Reaxys

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Rx-ID: 31549613 View in Reaxys 20/51 Yield

Rx-ID: 29536818 View in Reaxys 21/51 Yield

Conditions & References With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid, diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate in cyclohexane, Time= 72h, T= 50 °C , Molecular sieve, optical yield given as percent ee Wakchaure, Vijay N.; Zhou, Jian; Hoffmann, Sebastian; List, Benjamin; Angewandte Chemie - International Edition; vol. 49; nb. 27; (2010); p. 4612 - 4614 View in Reaxys

Rx-ID: 29716925 View in Reaxys 22/51 Yield

Conditions & References With Gln93Asn/Pro94Asp mutant phenylacetone monooxygenase, Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase, nicotinamide adenine dinucleotide, isopropyl alcohol in acetonitrile, T= 30 °C , pH= 8, aq. buffer, Baeyer-Villiger oxidation, optical yield given as percent ee, enantioselective reaction Wu, Sheng; Acevedo, Juan Pablo; Reetz, Manfred T.; Proceedings of the National Academy of Sciences of the United States of America; vol. 107; nb. 7; (2010); p. 2775 - 2780 View in Reaxys

Rx-ID: 28537862 View in Reaxys 23/51 Yield

Conditions & References With potassium bromide in water, T= 20 °C , optical yield given as percent ee

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Takenaga, Naoko; Goto, Akihiro; Yoshimura, Misaki; Fujioka, Hiromichi; Dohi, Toshifumi; Kita, Yasuyuki; Tetrahedron Letters; vol. 50; nb. 26; (2009); p. 3227 - 3229 View in Reaxys

Rx-ID: 29153828 View in Reaxys 24/51 Yield

Conditions & References With phenylacetone monooxygenase Pro440Phe mutant, secondary alcohol dehydrogenase, NADP, isopropyl alcohol in acetonitrile, T= 30 °C , pH= 8, aq. buffer, Enzymatic reaction, Baeyer-Villiger oxidation, Kinetics, optical yield given as percent ee, enantioselective reaction Reetz, Manfred T.; Wu, Sheng; Journal of the American Chemical Society; vol. 131; nb. 42; (2009); p. 15424 15432 View in Reaxys

Rx-ID: 28154848 View in Reaxys 25/51 Yield

Conditions & References With (S)-{3,3'-bis(2,4,6-triisopropylphenyl)-1,1'-binaphthalen-2,2'-yl}-N-triflyl-thiophosphoramide, acetic acid in toluene, Time= 6h, T= 20 °C , Inert atmosphere, optical yield given as percent ee, enantioselective reaction Cheol, Hong Cheon; Yamamoto, Hisashi; Journal of the American Chemical Society; vol. 130; nb. 29; (2008); p. 9246 - 9247 View in Reaxys

Rx-ID: 28154865 View in Reaxys 26/51 Yield

Conditions & References With (S)-{3,3'-bis(2,4,6-triisopropylphenyl)-1,1'-binaphthalen-2,2'-yl}-N-triflyl-thiophosphoramide, acetic acid in toluene, Time= 8h, T= 20 °C , Inert atmosphere, optical yield given as percent ee, enantioselective reaction Cheol, Hong Cheon; Yamamoto, Hisashi; Journal of the American Chemical Society; vol. 130; nb. 29; (2008); p. 9246 - 9247 View in Reaxys

Rx-ID: 11229563 View in Reaxys 27/51 Yield

Conditions & References With ethylenediaminetetraacetic acid, oxygen, flavin adenine dinucleotide, NADP in water, T= 30 °C , pH= 7.4, Irradiation, kinetic resolution, Baeyer-Villiger oxidative reaction

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Hollmann, Frank; Taglieber, Andreas; Schulz, Frank; Reetz, Manfred T.; Angewandte Chemie - International Edition; vol. 46; nb. 16; (2007); p. 2903 - 2906 View in Reaxys

I O

Rx-ID: 11203845 View in Reaxys 28/51 Yield

Conditions & References Multistep reaction. Title compound not separated from byproducts. Soorukram, Darunee; Knochel, Paul; Angewandte Chemie - International Edition; vol. 45; nb. 22; (2006); p. 3686 3689 View in Reaxys

H 2N H

H N H

NH 2

Rx-ID: 9641507 View in Reaxys 29/51 Yield

Conditions & References

40 %

With n-butyllithium in tetrahydrofuran, hexane, Time= 6h, T= 0 - 20 °C , Haller-Bauer reaction Ishihara, Kazuaki; Yano, Takayuki; Organic Letters; vol. 6; nb. 12; (2004); p. 1983 - 1986 View in Reaxys

Rx-ID: 4768691 View in Reaxys 30/51 Yield 100 %

Conditions & References With tin(IV) chloride, (R,R)-(-)-2-benzyloxy-1,2-bis[3,5-bis(trifluoromethyl)phenyl]ethanol in hexane, dichloromethane, Time= 1h, T= -78 °C Ishihara, Kazuaki; Nakashima, Daisuke; Hiraiwa, Yukihiro; Yamamoto, Hisashi; Journal of the American Chemical Society; vol. 125; nb. 1; (2003); p. 24 - 25 View in Reaxys With (R)-Lewis acid (SnCl4) assisted chiral Bronsted acid from (R)-binaphthol monomethyl ether in toluene, T= -78 °C Ishihara, Kazuaki; Ishida, Yuji; Nakamura, Shingo; Yamamoto, Hisashi; Synlett; vol. 1997; nb. 7; (1997); p. 758 - 760 View in Reaxys

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O O

Rx-ID: 8540900 View in Reaxys 31/51 Yield

Conditions & References

90 %

Stage 1: With methyllithium, lithium bromide, Metallation Stage 2: With chiral α-sulfinyl alcohol, T= -50 °C , protonation Asensio, Gregorio; Cuenca; Gavina; Medio-Simon, Mercedes; Tetrahedron Letters; vol. 40; nb. 20; (1999); p. 3939 - 3940 View in Reaxys

85 %

Stage 1: With methyllithium lithium bromide in diethyl ether, Time= 0.5h, T= 20 °C Stage 2: With (2S)-3,3,3-trifluoro-1-(4-methylphenylsulphinyl)-2-propanol in diethyl ether, dichloromethane, Time= 1.5h, T= -78 °C Asensio, Gregorio; Cuenca, Ana; Rodriguez, Nuria; Medio-Simon, Mercedes; Tetrahedron Asymmetry; vol. 14; nb. 24; (2003); p. 3851 - 3855 View in Reaxys

H HO OH

OH O

Rx-ID: 9431461 View in Reaxys 32/51 Yield

Conditions & References

64 %

With lead(IV) acetate in benzene, Time= 0.5h, T= 0 °C Kandula, SubbaRao V.; Puranik, Vedavati G.; Kumar, Pradeep; Tetrahedron Letters; vol. 44; nb. 27; (2003); p. 5015 - 5017 View in Reaxys

O HO

Rx-ID: 14201305 View in Reaxys 33/51 Yield

Conditions & References Reaction Steps: 5 1: 74 percent / mCPBA / CH2Cl2 / 4 h / 10 °C 2: 95 percent / Jones' reagent / acetone / 0.5 h / 20 °C 3: 90 percent / Et2AlCl / CH2Cl2 / 3 h / 0 °C 4: 65 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 5: Pb(OAc)4 / benzene / 0.5 h / 0 °C With lead(IV) acetate, lithium aluminium tetrahydride, jones' reagent, diethylaluminium chloride, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, dichloromethane, acetone, benzene, 3: Diels-Alder reaction Kandula, SubbaRao V.; Puranik, Vedavati G.; Kumar, Pradeep; Tetrahedron Letters; vol. 44; nb. 27; (2003); p. 5015 - 5017 View in Reaxys

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OH O

Rx-ID: 14201358 View in Reaxys 34/51 Yield

Conditions & References Reaction Steps: 4 1: 95 percent / Jones' reagent / acetone / 0.5 h / 20 °C 2: 90 percent / Et2AlCl / CH2Cl2 / 3 h / 0 °C 3: 65 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 4: Pb(OAc)4 / benzene / 0.5 h / 0 °C With lead(IV) acetate, lithium aluminium tetrahydride, jones' reagent, diethylaluminium chloride in tetrahydrofuran, dichloromethane, acetone, benzene, 2: Diels-Alder reaction Kandula, SubbaRao V.; Puranik, Vedavati G.; Kumar, Pradeep; Tetrahedron Letters; vol. 44; nb. 27; (2003); p. 5015 - 5017 View in Reaxys

O O

Rx-ID: 14201363 View in Reaxys 35/51 Yield

Conditions & References Reaction Steps: 3 1: 90 percent / Et2AlCl / CH2Cl2 / 3 h / 0 °C 2: 65 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 3: Pb(OAc)4 / benzene / 0.5 h / 0 °C With lead(IV) acetate, lithium aluminium tetrahydride, diethylaluminium chloride in tetrahydrofuran, dichloromethane, benzene, 1: Diels-Alder reaction Kandula, SubbaRao V.; Puranik, Vedavati G.; Kumar, Pradeep; Tetrahedron Letters; vol. 44; nb. 27; (2003); p. 5015 - 5017 View in Reaxys

H H

O H

Rx-ID: 14202123 View in Reaxys 36/51 Yield

Conditions & References Reaction Steps: 2 1: 65 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 2: Pb(OAc)4 / benzene / 0.5 h / 0 °C With lead(IV) acetate, lithium aluminium tetrahydride in tetrahydrofuran, benzene Kandula, SubbaRao V.; Puranik, Vedavati G.; Kumar, Pradeep; Tetrahedron Letters; vol. 44; nb. 27; (2003); p. 5015 - 5017 View in Reaxys

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O O

Rx-ID: 4676476 View in Reaxys 37/51 Yield

Conditions & References With samarium diiodide, (R)-2,2'-dilt;(S)-2-hydroxy-2-phenylethoxygt;-1,1'-binaphthyl in tetrahydrofuran, Time= 0.5h, Ambient temperature, effect of different chiral proton sources, Product distribution Nakamura, Yutaka; Takeuchi, Seiji; Ohgo, Yoshiaki; Yamaoka, Makoto; Yoshida, Akihiro; Mikami, Koichi; Tetrahedron Letters; vol. 38; nb. 15; (1997); p. 2709 - 2712 View in Reaxys With samarium diiodide, (S)-2,2'-dilt;(R)-2-(o-chlorophenyl)-2-hydroxyethoxygt;-1,1'-binaphthyl in tetrahydrofuran, Time= 0.5h, Ambient temperature, Yield given. Yields of byproduct given. Title compound not separated from byproducts Nakamura, Yutaka; Takeuchi, Seiji; Ohgo, Yoshiaki; Yamaoka, Makoto; Yoshida, Akihiro; Mikami, Koichi; Tetrahedron Letters; vol. 38; nb. 15; (1997); p. 2709 - 2712 View in Reaxys With samarium diiodide, (R,R)-lt;PhCH(OH)CH2N(CH2Ph)CH2gt;2 in tetrahydrofuran, Time= 0.5h, Ambient temperature, Yield given. Yields of byproduct given. Title compound not separated from byproducts Mikami, Koichi; Yamaoka, Makoto; Yoshida, Akihiro; Nakamura, Yutaka; Takeuchi, Seiji; Ohgo, Yoshiaki; Synlett; nb. 6; (1998); p. 607 - 608 View in Reaxys With samarium diiodide, (R)-2,2'-dilt;(S)-2-hydroxy-2-phenylethoxygt;-1,1'-binaphthyl in tetrahydrofuran, Time= 2h, T= -45 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Nakamura, Yutaka; Takeuchi, Seiji; Ohgo, Yoshiaki; Yamaoka, Makoto; Yoshida, Akihiro; Mikami, Koichi; Tetrahedron Letters; vol. 38; nb. 15; (1997); p. 2709 - 2712 View in Reaxys With samarium diiodide, (R)-2,2'-dilt;(S)-2-hydroxy-2-phenylethoxygt;-1,1'-binaphthyl in tetrahydrofuran, Time= 2h, T= -45 °C , enantioselectivity, various substrates and chiral proton source under different reaction conditions, Product distribution Nakamura, Yutaka; Takeuchi, Seiji; Ohgo, Yoshiaki; Yamaoka, Makoto; Yoshida, Akihiro; Mikami, Koichi; Tetrahedron; vol. 55; nb. 15; (1999); p. 4595 - 4620 View in Reaxys With samarium diiodide, N,N'-dilt;(S)-hydroxy-2-phenylethylgt;-N,N'-di(benzyl)ethylenediamine in tetrahydrofuran, Time= 0.5h, Ambient temperature, Yield given, Yields of byproduct given. Title compound not separated from byproducts Nakamura, Yutaka; Takeuchi, Seiji; Ohgo, Yoshiaki; Yamaoka, Makoto; Yoshida, Akihiro; Mikami, Koichi; Tetrahedron; vol. 55; nb. 15; (1999); p. 4595 - 4620 View in Reaxys With samarium diiodide, (R)-2,2'-dilt;(S)-2-hydroxy-2-phenylethoxygt;-1,1'-binaphthyl in tetrahydrofuran, Time= 2h, T= -45 °C , Yield given, Yields of byproduct given. Title compound not separated from byproducts Nakamura, Yutaka; Takeuchi, Seiji; Ohgo, Yoshiaki; Yamaoka, Makoto; Yoshida, Akihiro; Mikami, Koichi; Tetrahedron; vol. 55; nb. 15; (1999); p. 4595 - 4620 View in Reaxys With samarium diiodide, (R,S)-FDHPEB in tetrahydrofuran, Time= 2h, T= -45 °C , chiral protonation, Title compound not separated from byproducts Nakamura, Yutaka; Takeuchi, Seiji; Ohgo, Yoshiaki; Curran, Dennis P.; Tetrahedron; vol. 56; nb. 3; (2000); p. 351 - 356

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View in Reaxys

O O

Rx-ID: 8778824 View in Reaxys 38/51 Yield

Conditions & References Stage 1: With sodium methylate in methanol, T= 0 °C Stage 2: With sulfuric acid in methanol, T= -40 °C Hayashi; Senda; Ogasawara; Journal of the American Chemical Society; vol. 122; nb. 43; (2000); p. 10716 - 10717 View in Reaxys

O Cl

Rx-ID: 4675156 View in Reaxys 39/51 Yield

Conditions & References With samarium diiodide, (R)-2,2'-dilt;(S)-2-hydroxy-2-phenylethoxygt;-1,1'-binaphthyl in tetrahydrofuran, Time= 2h, T= -45 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Nakamura, Yutaka; Takeuchi, Seiji; Ohgo, Yoshiaki; Yamaoka, Makoto; Yoshida, Akihiro; Mikami, Koichi; Tetrahedron Letters; vol. 38; nb. 15; (1997); p. 2709 - 2712 View in Reaxys With samarium diiodide, (R)-2,2'-dilt;(S)-2-hydroxy-2-phenylethoxygt;-1,1'-binaphthyl in tetrahydrofuran, Time= 2h, T= -45 °C , Yield given, Yields of byproduct given. Title compound not separated from byproducts Nakamura, Yutaka; Takeuchi, Seiji; Ohgo, Yoshiaki; Yamaoka, Makoto; Yoshida, Akihiro; Mikami, Koichi; Tetrahedron; vol. 55; nb. 15; (1999); p. 4595 - 4620 View in Reaxys

O O O

Rx-ID: 4698630 View in Reaxys 40/51 Yield

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O Br

Rx-ID: 5146489 View in Reaxys 41/51 Yield

Conditions & References With samarium diiodide, (R)-2,2'-dilt;(S)-2-hydroxy-2-phenylethoxygt;-1,1'-binaphthyl in tetrahydrofuran, Time= 2h, T= -45 °C , Yield given, Yields of byproduct given. Title compound not separated from byproducts Nakamura, Yutaka; Takeuchi, Seiji; Ohgo, Yoshiaki; Yamaoka, Makoto; Yoshida, Akihiro; Mikami, Koichi; Tetrahedron; vol. 55; nb. 15; (1999); p. 4595 - 4620 View in Reaxys

Rx-ID: 16387651 View in Reaxys 42/51 Yield

Conditions & References Reaction Steps: 2 1: 19 percent / CrO3 / 0.5 h / 80 °C 2: SmI2, (R)-2,2'-di<(S)-2-hydroxy-2-phenylethoxy>-1,1'-binaphthyl / tetrahydrofuran / 2 h / -45 °C With chromium(VI) oxide, samarium diiodide, (R)-2,2'-dilt;(S)-2-hydroxy-2-phenylethoxygt;-1,1'-binaphthyl in tetrahydrofuran Nakamura, Yutaka; Takeuchi, Seiji; Ohgo, Yoshiaki; Yamaoka, Makoto; Yoshida, Akihiro; Mikami, Koichi; Tetrahedron; vol. 55; nb. 15; (1999); p. 4595 - 4620 View in Reaxys Reaction Steps: 3 1: 48 percent HBr / CHCl3 / 0.5 h / Ambient temperature 2: Jones reagent / acetone / 1 h / 0 °C 3: SmI2, (R)-2,2'-di<(S)-2-hydroxy-2-phenylethoxy>-1,1'-binaphthyl / tetrahydrofuran / 2 h / -45 °C With jones reagent, samarium diiodide, (R)-2,2'-dilt;(S)-2-hydroxy-2-phenylethoxygt;-1,1'-binaphthyl, hydrogen bromide in tetrahydrofuran, chloroform, acetone Nakamura, Yutaka; Takeuchi, Seiji; Ohgo, Yoshiaki; Yamaoka, Makoto; Yoshida, Akihiro; Mikami, Koichi; Tetrahedron; vol. 55; nb. 15; (1999); p. 4595 - 4620 View in Reaxys Reaction Steps: 3 1: HCl 2: Jones reagent / acetone / 1 h / 0 °C 3: SmI2, (R)-2,2'-di<(S)-2-hydroxy-2-phenylethoxy>-1,1'-binaphthyl / tetrahydrofuran / 2 h / -45 °C With hydrogenchloride, jones reagent, samarium diiodide, (R)-2,2'-dilt;(S)-2-hydroxy-2-phenylethoxygt;-1,1'-binaphthyl in tetrahydrofuran, acetone Nakamura, Yutaka; Takeuchi, Seiji; Ohgo, Yoshiaki; Yamaoka, Makoto; Yoshida, Akihiro; Mikami, Koichi; Tetrahedron; vol. 55; nb. 15; (1999); p. 4595 - 4620 View in Reaxys

Rx-ID: 16408185 View in Reaxys 43/51

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Yield

Conditions & References Reaction Steps: 2 1: Jones reagent / acetone / 1 h / 0 °C 2: SmI2, (R)-2,2'-di<(S)-2-hydroxy-2-phenylethoxy>-1,1'-binaphthyl / tetrahydrofuran / 2 h / -45 °C With jones reagent, samarium diiodide, (R)-2,2'-dilt;(S)-2-hydroxy-2-phenylethoxygt;-1,1'-binaphthyl in tetrahydrofuran, acetone Nakamura, Yutaka; Takeuchi, Seiji; Ohgo, Yoshiaki; Yamaoka, Makoto; Yoshida, Akihiro; Mikami, Koichi; Tetrahedron; vol. 55; nb. 15; (1999); p. 4595 - 4620 View in Reaxys

Rx-ID: 16408187 View in Reaxys 44/51 Yield

Rx-ID: 5023240 View in Reaxys 45/51 Yield

Conditions & References Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Ishihara, Kazuaki; Nakamura, Hiroko; Nakamura, Shingo; Yamamoto, Hisashi; Journal of Organic Chemistry; vol. 63; nb. 19; (1998); p. 6444 - 6445 View in Reaxys

Rx-ID: 4807772 View in Reaxys 46/51 Yield

Conditions & References With dimethylsulfide, ozone, Multistep reaction Ishihara, Kazuaki; Ishida, Yuji; Nakamura, Shingo; Yamamoto, Hisashi; Synlett; vol. 1997; nb. 7; (1997); p. 758 - 760 View in Reaxys

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Rx-ID: 17176444 View in Reaxys 47/51 Yield

Conditions & References Reaction Steps: 2 1: (R)-Lewis acid (SnCl4) assisted chiral Bronsted acid from (R)-binaphthol monomethyl ether / CH2Cl2 / 1 h / -90 °C 2: 1.) O3; 2.) Me2S With dimethylsulfide, (R)-Lewis acid (SnCl4) assisted chiral Bronsted acid from (R)-binaphthol monomethyl ether, ozone in dichloromethane Ishihara, Kazuaki; Ishida, Yuji; Nakamura, Shingo; Yamamoto, Hisashi; Synlett; vol. 1997; nb. 7; (1997); p. 758 - 760 View in Reaxys

Rx-ID: 4097795 View in Reaxys 48/51 Yield

Conditions & References With (R)-binaphthol, tin(IV) chloride in toluene, Time= 1h, T= -78 °C , Yield given Ishihara, Kazuaki; Kaneeda, Masanobu; Yamamoto, Hisashi; Journal of the American Chemical Society; vol. 116; nb. 24; (1994); p. 11179 - 11180 View in Reaxys

E N

Rx-ID: 4107677 View in Reaxys 49/51 Yield

Conditions & References With 3,3-dimethyldioxirane in acetone, Time= 24h, Ambient temperature, Yield given Murakata, Masatoshi; Imai, Megumi; Tamura, Masafumi; Hoshino, Osamu; Tetrahedron: Asymmetry; vol. 5; nb. 10; (1994); p. 2019 - 2024 View in Reaxys O

N E

Rx-ID: 18119384 View in Reaxys 50/51 Yield

Conditions & References Reaction Steps: 2 1: butan-1-ol; diisopropyl ether / 54 h / Ambient temperature; lipase from Rhizopus javanicus 2: dimethyldioxirane / acetone / 24 h / Ambient temperature With 3,3-dimethyldioxirane in di-isopropyl ether, acetone, butan-1-ol

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Murakata, Masatoshi; Imai, Megumi; Tamura, Masafumi; Hoshino, Osamu; Tetrahedron: Asymmetry; vol. 5; nb. 10; (1994); p. 2019 - 2024 View in Reaxys

Si Cl

Rx-ID: 1683408 View in Reaxys 51/51 Yield

Conditions & References With N,N,N,N,N,N-hexamethylphosphoric triamide in tetrahydrofuran, Time= 0.833333h, T= -105 °C , The portion of added chiral lithium amide was varied., Product distribution Kim; Kawasaki; Nakajima; Koga; Tetrahedron Letters; vol. 30; nb. 47; (1989); p. 6537 - 6540 View in Reaxys With N,N,N,N,N,N-hexamethylphosphoric triamide in tetrahydrofuran, Time= 0.833333h, T= -105 °C , Yield given. Further byproducts given. Yields of byproduct given Kim; Kawasaki; Nakajima; Koga; Tetrahedron Letters; vol. 30; nb. 47; (1989); p. 6537 - 6540 View in Reaxys

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