Dimethylsilyl ketene acetal as a nucleophile in asymmetric Michael reaction: Enhanced enantioselectivity in oxazaborolidinone-catalyzed reaction

被引：33

作者：

Harada, T ^{[1
]}

Adachi, S ^{[1
]}

Wang, XW ^{[1
]}

机构：

[1] Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6068585, Japan

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 26期

关键词：

D O I：

10.1021/ol048071g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dimethylsilanyl [Me2Si(H)] ketene SO-acetal 6b is an effective nucleophile that retards the undesirable Si+-catalyzed racemic pathway in the oxazaborolidinone-catalyzed asymmetric Michael reaction. Through the further suppression of the Si+-catalyzed pathway by carrying out the reaction in the presence of 2,6-diisopropylphenol and t-BuOMe as additives, enantioselectivity up to 98% ee could be achieved for a variety of acyclic enones.

引用

页码：4877 / 4879

页数：3

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