Horner-Wadsworth-Emmons modification for Ramirez gem-dibromoolefination of aldehydes and ketones using P(Oi-Pr)3

被引：50

作者：

Fang, Yuan-Qing ^{[1
]}

Lifchits, Olga ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Chem Lab, Toronto, ON M5S 3H6, Canada

来源：

SYNLETT | 2008年 / 03期

关键词：

olefination; phosphite; Horner-Wadsworth-Emmons reaction; aldehydes; ketones;

D O I：

10.1055/s-2008-1032045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple procedure for the use of triisopropylphosphite in the Ramirez olefination is described. This reagent is equally or more reactive than PPh(3) toward aldehydes and ketones in the gem-dibromoolefination of aldehydes and ketones. Under the reaction conditions, an alpha-bromoketone gave a novel tribromomethyl-substituted oxirane product in good yield. The substrate-dependent nature of this reaction suggests that this Horner-Wadsworth-Emmons equivalent of the Ramirez gem-dibromoolefination reaction proceeds through an ionic mechanism.

引用

页码：413 / 417

页数：5

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