Asymmetric Synthesis XVIII. Preparation of Chiral 1,2-diamines via the CN(R,S) Method. Application to the Synthesis of an Analogue of Tetraponerine.

Article abstract of DOI:10.1016/S0040-4039(01)93468-9

The reaction of organo-lithium or cuprate derivatives towards the cyano group of 2-cyano-6-phenyloxazolopiperidine synthon 1 gives an imine which is reduced to a primary amine with a remarkable stereoselectivity.An application of this reaction to the synt