ENZYME-MEDIATED ENANTIOFACE-DIFFERENTIATING HYDROLYSIS OF ALPHA-SUBSTITUTED CYCLOALKANONE ENOL ESTERS

被引：90

作者：

MATSUMOTO, K ^{[1
]}

TSUTSUMI, S ^{[1
]}

IHORI, T ^{[1
]}

OHTA, H ^{[1
]}

机构：

[1] KEIO UNIV,FAC SCI & TECHNOL,DEPT CHEM,HIYOSHI 3-14-1,KOHOKU KU,YOKOHAMA,KANAGAWA 223,JAPAN

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1990年 / 112卷 / 26期

关键词：

D O I：

10.1021/ja00182a020

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new type of enzymatic hydrolysis, enantioface-differentiating hydrolysis of enol esters, is disclosed. As a result of screening, Pichia miso IAM 4682, a type of yeast, was selected as the best strain to perform the enantioselective hydrolysis of enol esters to give alpha-chiral ketones. For example, incubation of 1-acetoxy-2-methylcyclohexene (4a) with P. miso afforded (S)-2-methylcyclohexanone (5) in high optical yield. This enzymatic hydrolysis is applicable to various alpha-substituted cycloalkanone enol esters, and thereby chiral six-, eight-, ten-, and twelve-membered-ring ketones of 70-96% enantiomeric excess (ee) are easily prepared.

引用

页码：9614 / 9619

页数：6

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