2-Ethynylaziridines as chiral carbon nucleophiles: Stereoselective synthesis of 1,3-amino alcohols with three stereocenters via allenylindium reagents bearing a protected amino group

被引：51

作者：

Ohno, H ^{[1
]}

Hamaguchi, H ^{[1
]}

Tanaka, T ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 05期

关键词：

D O I：

10.1021/jo005756v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allenylindium reagents bearing a protected amino group were effectively prepared from N-protected 3-alkyl-2-ethynylaziridines by treatment with InI in the presence of Pd(PPh3)(4) and H2O. Stereo-selective addition of the allenylindium to aliphatic or aromatic aldehydes affords 1,3-amino alcohols bearing three contiguous chiral centers: while 2,3-trans-2-ethynylaziridines yield syn,syn-2-ethynyl-1,3-amino alcohols predominantly, 2,3-cis-aziridines give anti,syn isomers selectively. Synthesis of highly substituted ethynylazetidines is also described.

引用

页码：1867 / 1875

页数：9

共 68 条

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