Issue 20, 1999

Convenient syntheses of chiral 3-substituted 2-ethynylaziridines

Abstract

Two convenient methods for the synthesis of chiral 2-ethynylaziridines from natural α-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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1999, 2949-2962

Convenient syntheses of chiral 3-substituted 2-ethynylaziridines

H. Ohno, A. Toda, Y. Takemoto, N. Fujii and T. Ibuka, J. Chem. Soc., Perkin Trans. 1, 1999, 2949 DOI: 10.1039/A905027B

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