NUCLEOPHILIC OPENING OF CHIRAL BIS-AZIRIDINES: A ROUTE TO ENANTIOMERICALLY PURE α-AMINO ACIDS AND POLYSUBSTITUTED PIPERIDINES

Article abstract of DOI:10.1016/S0040-4039(00)95507-2

Suitably protected chiral functionalised bis-aziridines, prepared from D-mannitol, are opened by various organometallic reagents ( organomagnesium, -lithium and -copper derivatives ) as well as by heteronucleophiles (N3(1-), Br(1-), Cl(1-), HS(1-), PhS(1-)).Orientation of the reaction toward diopening (route to enantiomerically pure α-amino acids) or toward heterocyclisation (route to chiral, polysubstituted piperidines) is influenced, notably, by the nature of the N-protecting group and of the nucleophile and by the presence or not of Lewis acids.