N-heterocyclic carbene-initiated α-acylvinyl anion reactivity:: Additions of α-hydroxypropargylsilanes to aldehydes

被引：41

作者：

Reynolds, Troy E. ^{[1
]}

Stern, Charlotte A. ^{[1
]}

Scheidt, Karl A. ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 13期

关键词：

D O I：

10.1021/ol0710515

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly substituted alpha,beta-unsaturated ketones are prepared by the N-heterocyclic carbene-initiated addition of alpha-hydroxypropargylsilanes to aldehydes. This strategy serves as a highly efficient alternative to the standard Morita-Baylis-Hillman (MBH) approaches for these types of compounds. In contrast to the MBH reaction, different substitution in the beta-position of the product (R-1) can be accommodated in moderate to excellent yields with a high degree of control over the resulting alkene.

引用

页码：2581 / 2584

页数：4

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