Stereoselective synthesis of nonracemic 1,3-amino alcohols from chiral 2-vinylaziridines by InP-Pd(0)-promoted metalation

被引：38

作者：

Takemoto, Y ^{[1
]}

Anzai, M ^{[1
]}

Yanada, R ^{[1
]}

Fujii, N ^{[1
]}

Ohno, H ^{[1
]}

Ibuka, T ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 09期

关键词：

indium and compounds; umpolung; amino alcohol; allylmetal; nucleophilic addition;

D O I：

10.1016/S0040-4039(00)02334-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of optically active 3-alkyl-2-vinylaziridines 1, 8 and 9 and allylic acetates 10 and 11 with InI in the presence of Pd(PPh3)(4) gives rise to chiral allylindiums bearing an amino group at the delta -position, which react with several aldehydes in highly regio- and stereoselective manner to afford the syn,syn-2-vinyl-1,3-amino alcohols 2a, 5a-7a and 12a-14a possessing three contiguous chiral centers in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：1725 / 1728

页数：4

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