Diphenylprolinol silyl ether as a catalyst in an enantioselective, catalytic, tandem Michael/Henry reaction for the control of four stereocenters

被引：219

作者：

Hayashi, Yujiro ^{[1
]}

Okano, Tsubasa ^{[1
]}

Aratake, Seiji ^{[1
]}

Hazelard, Damien ^{[1
]}

机构：

[1] Tokyo Univ Sci, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 26期

关键词：

domino reactions; Henry reactions; Michael reactions; organocatalysis; tandem reactions;

D O I：

10.1002/anie.200700909

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A choice of three: The tandem Michael/ Henry reaction of a nitroalkene and pentane-1,5-dial (generated in situ) proceeded efficiently when diphenylprolinol silyl ether was used as an organocatalyst to afford substituted nitrocyclohexanecarbaldehydes with high diastereo- and enantioselectivity (see scheme; TMS: trimethylsilyl). Isomerization under basic or acidic conditions diastereoselectively converts the product into two stereoisomers, without compromising the enantioselectivity. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4922 / 4925

页数：4

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