Stereoselective synthesis of chiral amino allenes by organocopper-mediated anti-SN2′-substitution reaction of chiral ethynylaziridines

被引：41

作者：

Ohno, H

Toda, A

Fujii, N

Takemoto, Y

Tanaka, T

Ibuka, T

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

[2] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

来源：

TETRAHEDRON | 2000年 / 56卷 / 18期

关键词：

allenes; aziridines; regiocontrol; stereoselection;

D O I：

10.1016/S0040-4020(00)00136-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral N-protected amino allenes have been synthesized from 3-alkyl-2-ethynylaziridines via organocopper-mediated reactions. Treatment of enantiomerically pure (2R,3S)-2,3-trans-3-alkyl-2-ethynylaziridines with RCu(CN)M (M=Li or MgX) in THF at -78 degrees C affords exclusively the expected (S,S)-amino allenes in high yields in a regio- and stereoselective manner. On the other hand, (2S,3S)-2,3-cis-3-alkyl-2-ethynylaziridines give stereoisomeric (S,R)-amino allenes in comparable high yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：2811 / 2820

页数：10

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