Enantioselective Michael Addition of Water

被引：22

作者：

Chen, Bi-Shuang ^{[1
]}

Resch, Verena ^{[1
,2
]}

Otten, Linda G. ^{[1
]}

Hanefeld, Ulf ^{[1
]}

机构：

[1] Delft Univ Technol, Afdeling Biotechnol, NL-2628 BL Delft, Netherlands

[2] Graz Univ, Inst Chem, A-8010 Graz, Austria

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 07期

基金：

奥地利科学基金会;

关键词：

biocatalysis; enantioselectivity; hydratases; Michael addition; water; ENOYL-COA HYDRATASE; ASYMMETRIC HYDRATION; CONJUGATE ADDITION; KINETIC RESOLUTION; FORMAL HYDRATION; ACID; STEREOCHEMISTRY; ENZYMES; 3-HYDROXYCYCLOHEXANONE; BIOSYNTHESIS;

D O I：

10.1002/chem.201405579

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective Michael addition using water as both nucleophile and solvent has to date proved beyond the ability of synthetic chemists. Herein, the direct, enantioselective Michael addition of water in water to prepare important beta-hydroxy carbonyl compounds using whole cells of Rhodococcus strains is described. Good yields and excellent enantioselectivities were achieved with this method. Deuterium labeling studies demonstrate that a Michael hydratase catalyzes the water addition exclusively with anti-stereochemistry.

引用

页码：3020 / 3030

页数：11

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