Lewis base activation of Lewis acids: Catalytic enantioselective glycolate aldol reactions

被引：41

作者：

Denmark, Scott E. ^{[1
]}

Chung, Won-Jin ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 10期

关键词：

1,2-diols; aldol reaction; diastereoselectivity; enantioselectivity; Lewis base catalysis;

D O I：

10.1002/anie.200705499

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Both syn- and anti-1,2-diols can be obtained with high diastereoselectivity and enantioselectivity from the properly substituted glycolate-derived silyl ketene acetals in the presence of SiCl 4 and a chiral bisphosphoramide catalyst (see scheme; TMS=trimethylsilyl, TBS=tert-butyldimethylsilyl). The sense of diastereoselectivity can be reversed by changing the size of the substituents on the silyl ketene acetals. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1890 / 1892

页数：3

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