Regioselective hydrogenolysis of enantiopure 2-benzyloxyaziridine 2-carboxy
lates represents a general method for the asymmetric synthesis of alpha -su
bstituted serines. The aziridines are readily prepared via an aza-Darzens r
eaction of the enolate of methyl 3-benzyloxy-2-bromopropanoate with an enan
tiopure sulfinimine (N-sulfinyl imine). (C) 2001 Elsevier Science Ltd. All
rights reserved.