Applications of aziridinium ions. Selective syntheses of alpha,beta-diamino esters, alpha-sulfanyl-beta-amino esters, beta-lactams, and 1,5-benzodiazepin-2-one

Academic Article
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publication date

  • November 2000

abstract

  • A variety of nucleophiles, including amines, thiolates, and alkoxides, were employed to open the aziridinium ions Az. The latter are opened stereospecifically and regioselectively at the C-3 position by a wide range of amines, and thiolate nucleophiles attack predominately at the C-2 position. Poor regioselectivities (ca. 1:1) were observed using nucleophiles derived from phenols, carboxylic acids, and imides. Base-mediated ring closure of the aziridinium opening products, from primary amines, gave beta-lactams and a 1, 5-benzodiazepin-2-one in high yields.