Intramolecular SN2 reaction α- to a trifluoromethyl group:: preparation of 1-cyano-2-trifluoromethylcyclopropane

被引：25
|
作者：
Katagiri, T [1 ]
Irie, M [1 ]
Uneyama, K [1 ]
机构：
[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan
来源：
TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 13期
关键词：
D O I：
10.1016/S0957-4166(99)00253-0
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The first intramolecular S(N)2 reaction of alpha-trifluoromethylated secondary alcohols by a carbanion is described. A stereoselective intramolecular cyclization of 3-substituted-3-cyano-1-trifluoromethylpropyl sulfonate via the cyano stabilized carbanion provides 1-substituted-1-cyano-2-trifluoromethylcyclopropanes in good yields. The product has the opposite configuration to the starting alcohol at the carbon attached to trifluoromethyl group, revealing the reaction takes place in S(N)2 manner with Walden inversion at the reaction center. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2583 / 2589
页数：7
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