Enantiocontrol in the bakers' yeast reduction of trifluoroacetylbiphenyl derivatives

被引：5

作者：

Fujisawa, T ^{[1
]}

Tanaka, S ^{[1
]}

Onogawa, Y ^{[1
]}

Shimizu, M ^{[1
]}

机构：

[1] Mie Univ, Dept Chem Mat, Tsu, Mie 5148507, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 10期

关键词：

bakers' yeast; asymmetric reduction; trifluoroacetylbiphenyls; methanethiosulfonate;

D O I：

10.1016/S0040-4039(99)00052-0

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 derivatives was examined in the presence of various esters of methanethiosulfonate. The yeast reduction of 4-bromo-4'-trifluoroacetylbiphenyl using the cyclohexylmethyl methanethiosulfonate resulted in the R product with the highest enantiomeric excess of 96% ee, which is compared with the reduction without the additive to give the corresponding alcohol with 84% ee. On the other hand, in the case of 4-hyrdoxy-4'-trifluoroacetylbiphenyl, the highest enantioselectivity was observed also using cyclohexylmethyl methanethiosulfonate to give the R-product with 90% ee, in contrast with the reduction without the additives to give the same product with 77% ee. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1953 / 1956

页数：4

共 58 条

[51] STEREOCHEMICAL CONTROL IN MICROBIAL REDUCTION .4. EFFECT OF CULTIVATION CONDITIONS ON THE REDUCTION OF BETA-KETO-ESTERS BY METHYLOTROPHIC YEASTS [J].