Convenient syntheses of chiral 3-substituted 2-ethynylaziridines

被引：39

作者：

Ohno, H ^{[1
]}

Toda, A ^{[1
]}

Takemoto, Y ^{[1
]}

Fujii, N ^{[1
]}

Ibuka, T ^{[1
]}

机构：

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

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 20期

关键词：

D O I：

10.1039/a905027b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two convenient methods for the synthesis of chiral 2-ethynylaziridines from natural alpha-amino acids are described. Sodium hydride-promoted aziridination of mesylates of 4-arylsulfonylamino-2-bromoalk-2-en-1-ols yields trans- 2-(1-bromovinyl)aziridines in a highly stereoselective manner, and subsequent dehydrobromination of the aziridines by potassium tert-butoxide gives separable stereoisomeric mixtures of trans- and cis-2-ethynylaziridines in enantiomerically pure forms (> 98% ee). Simple synthesis of 2-ethynylaziridines with high optical purities (91-98% ee) from chiral amino alcohols bearing an ethynyl group under Mitsunobu conditions is also presented.

引用

页码：2949 / 2962

页数：14

共 48 条

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