Stereoselective synthesis of 3-hydroxyazetidines via regioselective halogenation of 2,3-epoxyamines by using magnesium bromide

被引：16
作者：
Karikomi, M
Arai, K
Toda, T
机构：
[1] Department of Applied Chemistry, Faculty of Engineering, Utsunomiya University, Utsunomiya 321
来源：
TETRAHEDRON LETTERS | 1997年 / 38卷 / 34期
关键词：
D O I：
10.1016/S0040-4039(97)01360-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel stereoselective synthesis of 3-hydroxyazetidines starting from 2,3-hydroxyazetidines starting from 2,3-epoxyamines is described. Regioselectivity of the intramolecular cyclization of 2,3-epoxyamines is controlled by the use of magnesium bromide. The cyclization proceeds with retention of the stereochemistry, caused by double inversion of two sequential S(N)2 reactions of the epoxyamines. (C) 1997 Elsevier Science Ltd.
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页码：6059 / 6062
页数：4
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