114126-60-2Relevant academic research and scientific papers
NUCLEOPHILIC OPENING OF CHIRAL BIS-AZIRIDINES: A ROUTE TO ENANTIOMERICALLY PURE α-AMINO ACIDS AND POLYSUBSTITUTED PIPERIDINES
Dureault, A.,Tranchepain, I.,Greck, C.,Depezay, J-C.
, p. 3341 - 3344 (1987)
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.
Nucleophilic Opening of Chiral Bis(aziridines): A Route to Enantiomerically Pure α-Amino Aldehydes or Acids and Polysubstituted Piperidines
Dureault, Annie,Tranchepain, Isabelle,Depezay, Jean-Claude
, p. 5324 - 5330 (2007/10/02)
α-Amino aldehydes or acids can be obtained by nucleophilic opening of suitably protected chiral bis(aziridines) derived from D-mannitol.Nucleophiles consist of a wide range of organometallic and heteronucleophilic reagents.Reaction orientation toward bis-
