Synthesis of methyleneaminodipeptides via ring opening of a 2-(t-butoxycarbonylmethyl)aziridine derivative

The reactivity of 2-(t-butoxycarbonylmethyl)aziridine-1-carboxylic acid benzyl ester has been studied with various N-nucleophiles. The ring-opening reaction was always regioselective, the nucleophile attacking preferentially the less hindered carbon of the aziridine. The reaction was used to prepare a methyleneamino pseudodipeptide using the α-amine of a lysine ester.