Ring opening of 2-acylaziridines by acid chlorides

Y Kim, HJ Ha, H Yun, BK Lee, WK Lee

Index: Kim, Yongeun; Ha, Hyun-Joon; Yun, Hoseop; Lee, Baeck Kyoung; Lee, Won Koo Tetrahedron, 2006 , vol. 62, # 37 p. 8844 - 8849

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Citation Number: 31

Abstract

Good nucleophilicity of the ring nitrogen in chiral (2R, 1′ R)-2-acyl-(1′-phenylethyl) aziridines initiated the reaction with various acid chlorides to form the corresponding acylaziridinium ion intermediates whose rings were opened by the chloride anion to yield the β-amino-α-chlorocarbonyl compounds. The subsequent displacement of the chloride with the internal oxygen nucleophile originated from methylchloroformate, acetyl chloride, ...