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
收藏
页码：8175 / 8178
页数：4
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