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
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页码:2949 / 2962
页数:14
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