Studies into the asymmetric Meisenheimer rearrangement

被引：12

作者：

Buston, JEH

Coldham, I

Mulholland, KR

机构：

[1] Univ Exeter, Dept Chem, Exeter EX4 4QD, Devon, England

[2] SmithKline Beecham Pharmaceut, Harlow CM19 5AW, Essex, England

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(98)00191-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Oxidation of a variety of N-allyl prolinol derivatives gave amine N-oxides with complete diastereoselectivity. On warming, these amine N-oxides undergo [2,3]-Meisenheimer rearrangement to give O-allyl hydroxylamines, albeit with low diastereoselectivity. Attempts to promote asymmetric N-oxidation of N-allyl tertiary amines with a variety of asymmetric oxidants produced only racemic N-oxides. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：1995 / 2009

页数：15

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