Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides

被引：18

作者：

O'Brien, P ^{[1
]}

Towers, TD ^{[1
]}

Voith, M ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 44期

关键词：

epoxidation; diastereoselection; rearrangements; enantioselection;

D O I：

10.1016/S0040-4039(98)01821-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several N-mono- and diprotected alkenes have been prepared and the, stereoselectivity of their epoxidation has been investigated: N-monoprotected alkenes give cis epoxides preferentially (due to hydrogen bonding directed epoxidations) whereas N-diprotected alkenes produce trans epoxides exclusively (due to steric effects). Chiral lithium amide base-mediated rearrangement of a cis-monoprotected epoxide generated the corresponding amino-cyclopentenol in good yield and with an enantiomeric excess of 60%. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：8175 / 8178

页数：4

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