Recent Progress in Lewis Base Activation and Control of Stereoselectivity in the Additions of Trimethylsilyl Nucleophiles

被引：281

作者：

Gawronski, Jacek ^{[1
]}

Wascinska, Natalia ^{[1
]}

Gajewy, Jadwiga ^{[1
]}

机构：

[1] Adam Mickiewicz Univ, Dept Chem, Poznan, Poland

来源：

CHEMICAL REVIEWS | 2008年 / 108卷 / 12期

关键词：

D O I：

10.1021/cr800421c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Lewis base activation and control of stereoselectivity in the additions of trimethylsilyl nucleophiles was reported with their recent progress. Catalytic additions of trimethylsilyl nucleophiles offer a number of advantages compared to additions of ionic metal nucleophiles. These nucleophiles can prove as effective alternatives for proton nucleophiles in addition reactions to electrophiles as aldeydes, ketones, and nitrones. The role of Lewis base as an initiator or a true catalyst is central to understanding the stereochemical consequences of additions of silylated nucleophiles. The stereochemical outcome of a nucleophile addition reaction may depend on the structure of the alkoxide product, which is chiral but not necessarily homochiral. The development of more accessible (chiral) catalysts, used at lower molar loads, can help improve its industrial applications.

引用

页码：5227 / 5252

页数：26

共 365 条

[41] REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES [J].