High π-facial selectivity through chelation of magnesium ions in the DMD epoxidation of α,β-unsaturated imides with chiral pyrrolidinone auxiliaries

被引：16

作者：

Adam, W ^{[1
]}

Zhang, AM ^{[1
]}

机构：

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

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 01期

关键词：

chiral auxiliaries; dioxirane; epoxidation; mechanism; metal chelation;

D O I：

10.1002/ejoc.200300544

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

High diastereoselectivity, but of the opposite sense, is observed in the epoxidation (DMD or mCPBA) of alpha,beta-unsaturated imides equipped with pyrrolidinone-type chiral auxiliaries that bear either a hydroxymethyl or trityloxymethyl side chain. This unprecedented reversed pi-facial differentiation is promoted by chelation of a magnesium ion, which results in conformational control over the essential steric interactions. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

引用

页码：147 / 152

页数：6

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