Regio- and stereoselectivity in reactions of 2,3-cis- and trans-3-alkyl-2-vinylaziridines with organocopper reagents: Importance of 2,3-cis-stereochemistry in controlling selectivity

被引：32

作者：

Aoyama, H ^{[1
]}

Mimura, N ^{[1
]}

Ohno, H ^{[1
]}

Ishii, K ^{[1
]}

Toda, A ^{[1
]}

Tamamura, H ^{[1
]}

Otaka, A ^{[1
]}

Fujii, N ^{[1
]}

Ibuka, T ^{[1
]}

机构：

[1] KYOTO UNIV,GRAD SCH PHARMACEUT SCI,SAKYO KU,KYOTO 606,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 42期

关键词：

D O I：

10.1016/S0040-4039(97)01726-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By treatment with organocopper reagents, N-activated 2,3-cis-3-alkyl-2-vinylaziridines produced exclusively (E)-allyl amines in high yields, presumably via an anti-S(N)2' reaction pathway. On the other hand, under otherwise identical conditions, N-activated 2,3-trans-3-alkyl-2-vinylaziridines gave an 85-96:15-4 mixture of (E)- and (Z)-allyl amines. In reactions of certain N-activated 2,3-trans-3-alkyl-2-vinylaziridines, S(N)2 reaction products were obtained in only 2-3% yield. (C) 1997 Elsevier Science Ltd.

引用

页码：7383 / 7386

页数：4

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