Diastereoselective epoxidation of oxazolidine-substituted alkenes by dimethyldioxirane and m-chloroperbenzoic acid:: π-facial control through hydrogen bonding by the urea functionality

被引：20

作者：

Adam, W ^{[1
]}

Schambony, SB ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 01期

关键词：

D O I：

10.1021/ol006800w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A high diastereoselectivity (up to >98:2) is found for the DMD and m-CPBA epoxidations of chiral oxazolidine substituted olefins with a urea group. The selectivity is explained in terms of hydrogen bonding between the remote NH group of the urea functionality and the epoxidizing reagent. Methylation of the NH group prohibits hydrogen bonding, and a reversed selectivity is observed due to steric repulsion between the reagent and the urea functionality.

引用

页码：79 / 82

页数：4

共 36 条

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