Base-induced heterochiral dimerization of an oxiranyl carbaldimine:: Stereoselective synthesis of a highly functionalized aziridine

被引：24

作者：

Alickmann, D ^{[1
]}

Fröhlich, R ^{[1
]}

Wurthwein, EU ^{[1
]}

机构：

[1] Inst Organ Chem, D-48149 Munster, Germany

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 10期

关键词：

D O I：

10.1021/ol0158314

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of the oxiranyl carbaldimine with base (LDA or LDA/KOtBu) leads in an one-step procedure to the polyfunctionalized aziridine, This highly diastereoselective reaction is explained by a new type of an Aza-Darzens reaction, in which one enantiomer of the starting material is deprotonated to form an oxiranyl anion, which attacks the imine carbon atom of the other enantiomer (mutual kinetic resolution by double diastereofacial selection).

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页码：1527 / 1530

页数：4

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