Mimicry of polyketide synthases - Enantioselective 1,4-addition reactions of malonic acid half-thioesters to nitroolefins

被引：176

作者：

Lubkoll, Jana ^{[1
]}

Wennemers, Helma ^{[1
]}

机构：

[1] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 36期

关键词：

asymmetric synthesis; biomimetic synthesis cinchona; alkaloids; enzymes; organocatalysis;

D O I：

10.1002/anie.200702187

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Bifunctionality is the key for mimicking the active site of polyketide synthases with synthetic metal-free organocatalysts (see picture). Cinchona alkaloid derivatives bearing both a basic site and a urea moiety catalyze conjugate enantioselective addition reactions of malonic acid half thioesters (MAHTs) to nitroolefins with up to quantitative yields and selectivities up to 90% ee. (Chemical Equation Presented). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

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页码：6841 / 6844

页数：4

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