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

页码：9633 / 9640

页数：8

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