Synthesis of enantiopure substituted aziridines by diastereoselective N- bromocyclization and nucleophile-mediated regioselective opening

Article abstract of DOI:10.1016/S0040-4039(98)01109-5

Enantiopure β-substituted aziridines were prepared from (S)- phenylglycinol through a key N-bromocyclizatlon of an unsaturated iminoether. A total control of the regioselectivity was observed during the opening of these aziridines by various nucleophiles (N₃^-, H₂O, EtOH, Me₂CuLi).