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

Zhu, JiepingQuirion, Jean CharlesHusson, Henri Philippe2010-11-252010-11-252010-11-25198910.1016/S0040-4039(01)93468-9https://infoscience.epfl.ch/handle/20.500.14299/58586The 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)]tetraponerine analog; oxazolopiperidine phenylcyano synthon; synthon cyanophenyloxazolopiperidineAsymmetric synthesis. XVIII. Preparation of chiral 1,2-diamines via the CN(R,S) method. Application to the synthesis of an analog of tetraponerinetext::journal::journal article::research article