Tetrahedron Letters p. 3341 - 3344 (1987)
Update date:2022-07-29
Topics:
Dureault, A.
Tranchepain, I.
Greck, C.
Depezay, J-C.
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.
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