Ring opening of 2-acylaziridines by acid chlorides

초록

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 beta-amino-alpha-chlorocarbonyl compounds. The subsequent displacement of the chloride with the internal oxygen nucleophile originated from methylchloroformate, acetyl chloride, and methyl chlorooxoacetate yielded oxazolidin-2-ones, beta-amino-alpha-acetyloxypropionates, and morpholin-2,3-diones, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

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