Bridging between Organocatalysis and Biocatalysis: Asymmetric Addition of Acetaldehyde to ß-Nitrostyrenes Catalyzed by a Promiscuous Proline-Based Tautomerase

被引：73

作者：

Zandvoort, Ellen ^{[1
]}

Geertsema, Edzard M. ^{[1
]}

Baas, Bert-Jan ^{[1
]}

Quax, Wim J. ^{[1
]}

Poelarends, Gerrit J. ^{[1
]}

机构：

[1] Univ Groningen, Groningen Res Inst Pharm, Dept Pharmaceut Biol, NL-9713 AV Groningen, Netherlands

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 05期

基金：

欧洲研究理事会;

关键词：

catalytic promiscuity; enzyme catalysis; Michael addition; organocatalysis; tautomerases; ENANTIOSELECTIVE MICHAEL ADDITION; CARBON BOND FORMATION; 4-OXALOCROTONATE TAUTOMERASE; MANNICH; ALDOL; KNOEVENAGEL; ALDEHYDES; MALONATE; ENZYMES; KETONES;

D O I：

10.1002/anie.201107404

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Non-natural beauty: The enzyme 4-oxalocrotonate tautomerase (4-OT) promiscuously (i.e., with non-natural activity) catalyzes the Michael-type addition of acetaldehyde to nitrostyrene. Catalysis likely proceeds via enamine formation of the amino-terminal proline residue of 4-OT with acetaldehyde (see picture), reminiscent of organocatalysis. High stereoselectivity, low catalyst loading, and water as reaction medium characterize this methodology. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1240 / 1243

页数：4

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