New synthesis and ring opening of cis-3-alkylaziridine-2-carboxylates

Syntheses of cis-3-alkylaziridine-2-carboxylates including cis-3-benzyl- an d cis-3-phenylaziridine-2-carboxylates were achieved from the reaction of a lpha -aminonitrile and alkyldiazoacetate in the presence of a Lewis acid. A symmetric version of this reaction with the chiral alpha -methylbenzylamine was also successful for the preparation of chiral aziridines that were use d for the synthesis of various amino acids including homophenylalanine, bet a -amino-alpha -hydroxy acid, alpha,beta -diamino acid, and alpha -amino-be ta -hydroxy acid via regioselective aziridine ring openings. (C) 2001 Elsev ier Science Ltd. All rights reserved.