Aziridine mediated asymmetric synthesis of α-benzylserine and α-n-butylserine

Regioselective hydrogenolysis of enantiopure 2-benzyloxyaziridine 2-carboxylates represents a general method for the asymmetric synthesis of α-substituted serines. The aziridines are readily prepared via an aza-Darzens reaction of the enolate of methyl 3-benzyloxy-2-bromopropanoate with an enantiopure sulfinimine (N-sulfinyl imine).