Convenient syntheses of chiral 3-substituted 2-ethynylaziridines

H Ohno, A Toda, Y Takemoto, N Fujii…

文献索引：Ohno, Hiroaki; Toda, Ayako; Takemoto, Yoshiji; Fujii, Nobutaka; Ibuka, Toshiro Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 20 p. 2949 - 2962

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被引用次数: 38

摘要

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 ...