Asymmetric synthesis. XVIII. Preparation of chiral 1,2-diamines via the CN(R,S) method. Application to the synthesis of an analog of tetraponerine

The reaction or organo-lithium or cuprate derivs. towards the cyano group of 2-cyano-6-phenyloxazolopiperidine synthon I gives an imine which is reduced to a primary amine with a remarkable stereoselectivity. An application of this reaction to the synthesis of the tetraponerine analog II is presented. [on SciFinder (R)]