Anodic Cyanation of (S)-(-)-1-(1-Phenylethyl)piperidine: an Expeditious Synthesis of (S)-(+)-Coniine

A short and efficient asymmetric synthesis of enantiopure (S)-(+)-coniine is reported. Anodic cyanation of (-)-1-[(1S)-1-phenylethyl]piperidine, derived from [(1S)1-phenylethyl]amine, results in regioselective formation of the corresponding (alpha)-amino­nitrile, which was alkylated with propyl iodide to give a bifunc­tional derivative. The latter underwent a stereoselective reductive decyanation (80% de), the product of which was hydrogenolyzed to afforded (S)-(+)-coniine (99% ee) with an overall 35% yield from (-)-1-[(1S)-1-phenylethyl]piperidine.