Synlett

Anodic cyanation of (S)-(-)-1-(1-phenylethyl) piperidine: an expeditious synthesis of (S)-(+)-coniine

N Girard, L Pouchain, JP Hurvois, C Moinet

Index: Girard, Nicolas; Pouchain, Laurent; Hurvois, Jean-Pierre; Moinet, Claude Synlett, 2006 ,  # 11  p. 1679 - 1682

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Citation Number: 8

Abstract

Abstract 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 α-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 ...