Aziridine and azirine carboxylic esters

Abstract

A convenient synthesis of aziridine-2-carboxylic esters of high enantiopurity from the corresponding oxiranecarboxylic esters is described. Ring opening reactions of these aziridine esters with various nucleophilic agents constitute a versatile entrée to fianctionalized amino acid derivatives. The synthesis of 2H-azirine-2-carboxylic esters from aziridine-2-carboxylic esters by an eliminative reaction is reported. An alternative preparation of 2H-azirine-2-carboxylic esters involves an alkaloid mediated synthesis from the oxime tosylates of β-keto esters by a modified Neber reaction.