ASYMMETRIC SYNTHESIS XX. PREPARATION OF A NOVEL SPIROPIPERIDINE SYSTEM BY THE CN(R,S) METHOD.

Article abstract of DOI:10.1016/S0040-4039(01)93883-3

A novel spiropiperidine system i.e. an aza structural analog of histrionicotoxin has been constructed from 2-cyano-6-phenyloxazolopiperidine synthon 3.The suitable quaternary carbon was created by alkylation at the position α to the nitrile followed by transformation of the nitrile group into a primary amine.Final aminoreductive cyclisation gave the spiro system.