cis-selective aziridination of cis- or trans-α,β-unsaturated amides using diaziridine

被引：25

作者：

Hori, K ^{[1
]}

Sugihara, H ^{[1
]}

Ito, YN ^{[1
]}

Katsuki, T ^{[1
]}

机构：

[1] Kyushu Univ, Fac Sci, Dept Chem, Higashi Ku, Fukuoka 8128581, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 28期

关键词：

aziridines; diaziridines; amides; diastereoselection;

D O I：

10.1016/S0040-4039(99)00939-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aziridination of alpha,beta-unsaturated amides was effected by treatment with lithiated 3,3-pentamethylenediaziridine in high diastereoselectivity. cis-Aziridine was the predominant diastereomer irrespective of the geometry of the substrates. A stepwise mechanism, 1,4-addition of a lithiated diaziridine to alpha,beta-unsaturated amides and subsequent ring closure at the nitrogen atom was proposed to explain the unusual cis-selectivity. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5207 / 5210

页数：4

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