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

Syntheses of cis-3-alkylaziridine-2-carboxylates including cis-3-benzyl- and cis-3-phenylaziridine-2-carboxylates were achieved from the reaction of α-aminonitrile and alkyldiazoacetate in the presence of a Lewis acid. Asymmetric version of this reaction with the chiral α-methylbenzylamine was also successful for the preparation of chiral aziridines that were used for the synthesis of various amino acids including homophenylalanine, β-amino-α-hydroxy acid, α,β-diamino acid, and α-amino-β-hydroxy acid via regioselective aziridine ring openings.