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
收藏
页码：9293 / 9304
页数：12
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