New route to 4-aminocyclopent-2-en-1-ols: Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides

被引：40
|
作者：
Barrett, S [1 ]
O'Brien, P [1 ]
Steffens, HC [1 ]
Towers, TD [1 ]
Voith, M [1 ]
机构：
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
来源：
TETRAHEDRON | 2000年 / 56卷 / 49期
关键词：
amino alcohols; epoxidation; stereocontrol; nucleosides;
D O I：
10.1016/S0040-4020(00)00911-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new route for the asymmetric synthesis of 4-aminocyclopent-2-en-1-ols (90% ee) for carbocyclic nucleoside analogue synthesis is described. The approach involves the stereoselective preparation of cis 4-amino-substituted cyclopentene oxides and subsequent chiral base-mediated rearrangement to the corresponding allylic alcohols. Full details on the synthesis and stereoselectivity of epoxidation of 4-amino-substituted cyclopentenes are presented. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：9633 / 9640
页数：8
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