Practical two-step synthesis of an enantiopure aliphatic terminal (S)-epoxide based on reduction of haloalkanones with "Designer Cells"

被引：35

作者：

Berkessel, Albrecht ^{[1
]}

Rollmann, Claudia ^{[2
]}

Chamouleau, Francoise ^{[2
]}

Labs, Stefanie ^{[1
]}

May, Oliver ^{[2
]}

Groger, Harald ^{[2
,3
]}

机构：

[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

[2] Degussa AG, Serv Ctr Biocatalysis, D-63403 Hanau, Germany

[3] Univ Erlangen Nurnberg, Inst Organ Chem, D-91054 Erlangen, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 17-18期

关键词：

alcohols; asymmetric catalysis; enzyme catalysis; epoxides; halohydrins; reduction;

D O I：

10.1002/adsc.200700244

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A practical biocatalytic method for the synthesis of aliphatic P-halogenated (S)-alcohols as epoxide precursors by means of an enantioselective reduction of the corresponding ketones with recombinant whole cells, bearing an alcohol dehydrogenase and a glucose dehydrogenase, was developed. The biotransformations operate at high substrate concentrations of up to 208 g/L, and afford the (S)-beta-halohydrins with both high conversions of > 95 % and enantioselectivities of > 99 % ee. Base-induced cyclization of the P-halohydrin intermediates gave the desired (S)-epoxides in high yield and enantiomeric purity (> 99 % ee).

引用

页码：2697 / 2704

页数：8

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