Reactivity of substituted and unsubstituted diphenylphosphonium diylides towards carbonic acids derivatives.

被引：25

作者：

Cristau, HJ ^{[1
]}

Taillefer, M ^{[1
]}

机构：

[1] ENSCM, Chim Organ Lab, URA CNRS ESA 5076, F-34296 Montpellier 5, France

来源：

TETRAHEDRON | 1998年 / 54卷 / 08期

关键词：

D O I：

10.1016/S0040-4020(97)10360-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In order to further delimit the scope of application of diphenylphosphonium diylides, their reactivity towards carbonic acid derivatives was investigated. Non-stabilized diylides react with ethyl carbonate to give new monoylide intermediates which lead, by in situ Wittig reaction with carbonyl compounds, to the synthesis of alpha,beta-unsaturated esters or acids the double bond being di-or trisubstituted. The reaction proceeds in mild conditions and with high E stereoselectivity. Stabilized diylides are inactive towards carbonates but semi-stabilized diylides react with ethyl carbonate leading to the synthesis of non-functionalized alkenes instead of the alpha,beta-unsaturated esters or acids. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1507 / 1522

页数：16

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