Synthesis of enantiomerically pure trans aziridine-2-carboxylates by diastereoselective Gabriel-Cromwell reaction

被引：54

作者：

Cardillo, G ^{[1
]}

Gentilucci, L ^{[1
]}

Tomasini, C ^{[1
]}

CastejonBordas, MPV ^{[1
]}

机构：

[1] UNIV BOLOGNA,CNR,CSFM,I-40126 BOLOGNA,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 03期

关键词：

D O I：

10.1016/0957-4166(96)00071-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Benzyl aziridine-2-carboxylates have been obtained in high yield and selectivity by conjugate addition of ammonia to alpha,beta-unsaturated chiral imides followed by treatment with lithium benzyloxide. A ring-expansion of the aziridine to an oxazoline allowed the determination of the absolute stereochemistry for the newly formed stereogenic centres. (C) 1996 Elsevier Science Ltd

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页码：755 / 762

页数：8

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