New synthesis and cyclopropanation of α-phenylselanyl α,β-unsaturated ketones with non-stabilized phosphorus ylides

被引：23

作者：

Redon, Sebastien

Leleu, Stephane

Pannecoucke, Xavier

Franck, Xavier

Outurquin, Francis

机构：

[1] Univ Mt St Aignan, F-76131 Mont St Aignan, France

[2] INSA, CNRS, UMR 6014, COBRA IRCOF, F-76131 Mont St Aignan, France

来源：

TETRAHEDRON | 2008年 / 64卷 / 39期

关键词：

selenium; alpha-phenylselanyl enones; cyclopropane; dihydrofuran; conjugated dienes;

D O I：

10.1016/j.tet.2008.07.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method for the preparation of alpha-phenylselanyl enones is described. Phosphorus ylides react with these alpha-phenylselanyl enones in a 1,4-addition, leading to cyclopropanes and/or dihydrofurans, depending on the substitution pattern. This unusual reactivity is due to the phenylselanyl moiety, hindering the carbonyl of the enone and making it less prone to 1,2-additions or conjugate addition by electronic effects. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：9293 / 9304

页数：12