Strained silacycle-catalyzed asymmetric Diels-Alder cycloadditions: the first highly enantioselective silicon Lewis acid catalyst

被引：31

作者：

Kubota, Katsumi ^{[1
]}

Hamblett, Christopher L. ^{[1
]}

Wang, Xiaolun ^{[1
]}

Leighton, James L. ^{[1
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

TETRAHEDRON | 2006年 / 62卷 / 49期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

silicon; Lewis acid; catalyst; Diels-Alder; enantioselective;

D O I：

10.1016/j.tet.2006.06.076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first highly enantioselective silicon Lewis acid catalyst for an asymmetric organic transformation has been developed. The catalyst derives its activity from the strain induced in the silicon center by virtue of being constrained in a five-membered ring. A simple tridentate ligand has been developed and the derived chlorosilane complex catalyzes the Diels-Alder cycloaddition of methacrolein and cyclopentadiene with 94% ee. (c) 2006 Elsevier Ltd. All rights reserved.

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页码：11397 / 11401

页数：5

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