Olefination of ketones using a gold(III)-catalyzed Meyer-Schuster rearrangement

被引：179

作者：

Engel, Douglas A. ^{[1
]}

Dudley, Gregory B. ^{[1
]}

机构：

[1] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 18期

关键词：

D O I：

10.1021/ol0616743

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An atom-economical and efficient olefination strategy for ketones is described. Ethoxyacetylide addition followed by a gold-catalyzed Meyer Schuster rearrangement affords alpha,beta-unsaturated esters, generally in excellent overall yield from the starting ketones. The alkynophilicity of Au3+ promotes an interaction with the electron-rich acetylenes that catalyzes the Meyer-Schuster rearrangement selectively over other conceivable pathways.

引用

页码：4027 / 4029

页数：3