Asymmetric reductions of (trifluoroacetyl)biphenyl derivatives with bakers' yeast and with Geotrichum candidum acetone powder

被引：32

作者：

Fujisawa, T ^{[1
]}

Onogawa, Y ^{[1
]}

Sato, A ^{[1
]}

Mitsuya, T ^{[1
]}

Shimizu, M ^{[1
]}

机构：

[1] Mie Univ, Dept Chem Mat, Tsu, Mie 514, Japan

来源：

TETRAHEDRON | 1998年 / 54卷 / 17期

关键词：

D O I：

10.1016/S0040-4020(98)00144-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The bakers' yeast reduction of (trifluoroacetyl)biphenyl derivatives produces (R)-trifluoromethyl biphenylyl carbinols in high enantioselectivity, whereas the reduction of the same derivatives with Geotrichum candidum acetone powder gives the corresponding (S)-carbinols in excellent yields and enantioselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：4267 / 4276

页数：10

相关论文

共 43 条

[1] SELECTIVE REDUCTIONS .37. ASYMMETRIC REDUCTION OF PROCHIRAL KETONES WITH B-(3-PINANYL)-9-BORABICYCLO[3.3.1]NONANE [J].

BROWN, HC ;

PAI, GG .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1384-1394

[2] ASYMMETRIC REDUCTION OF TRIFLUOROMETHYL KETONES BY ACTIVELY FERMENTING YEAST [J].

BUCCIARELLI, M ;

FORNI, A ;

MORETTI, I ;

TORRE, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (11) :456-457

[3]

BUCCIARELLI M, 1983, J CHEM SOC CHEM COMM, P897

[4] ENANTIOSELECTIVE REDUCTION OF ARYL TRIFLUOROMETHYL KETONES WITH BINAL-H - PREPARATION OF 2,2,2-TRIFLUORO-1-(9-ANTHRYL)ETHANOL [J].

CHONG, JM ;

MAR, EK .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :893-896

[5] A NEW SYSTEM FOR CATALYTIC ENANTIOSELECTIVE REDUCTION OF ACHIRAL KETONES TO CHIRAL ALCOHOLS - SYNTHESIS OF CHIRAL ALPHA-HYDROXY ACIDS [J].

COREY, EJ ;

BAKSHI, RK .

TETRAHEDRON LETTERS, 1990, 31 (05) :611-614

[6] REMARKABLY EFFECTIVE AND SIMPLE SYNTHESES OF ENANTIOMERICALLY PURE SECONDARY CARBINOLS FROM ACHIRAL KETONES [J].

COREY, EJ ;

CHENG, XM ;

CIMPRICH, KA ;

SARSHAR, S .

TETRAHEDRON LETTERS, 1991, 32 (47) :6835-6838

[7] BAKERS-YEAST MEDIATED TRANSFORMATIONS IN ORGANIC-CHEMISTRY [J].

CSUK, R ;

GLANZER, BI .

CHEMICAL REVIEWS, 1991, 91 (01) :49-97

[8] STEREOCONTROLLED SYNTHESIS OF P-SUBSTITUTED TRIFLUOROMETHYLBENZYLIC ALCOHOL DERIVATIVES OF HIGH OPTICAL PURITY BY THE BAKERS-YEAST REDUCTION [J].

FUJISAWA, T ;

ICHIKAWA, K ;

SHIMIZU, M .

TETRAHEDRON-ASYMMETRY, 1993, 4 (06) :1237-1240

[9] HIGHLY STEREOCONTROLLED ACCESS TO TRIFLUOROMETHYLBENZYLIC ALCOHOLS POSSESSING P-SUBSTITUENTS BY THE BAKERS-YEAST REDUCTION [J].

FUJISAWA, T ;

SUGIMOTO, T ;

SHIMIZU, M .

TETRAHEDRON-ASYMMETRY, 1994, 5 (06) :1095-1098

[10] MICROBIOLOGICAL SYNTHESIS OF VARIOUSLY PROTECTED L-GLYCERALDEHYDES IN HIGH OPTICAL PURITY [J].

GUANTI, G ;

BANFI, L ;

NARISANO, E .

TETRAHEDRON LETTERS, 1986, 27 (30) :3547-3550

← 1 2 3 4 5 →