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

Nicolas Girard; Laurent Pouchain; Jean-Pierre Hurvois; Claude Moinet

doi:10.1055/s-2006-944214

LETTER

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

Nicolas Girard, Laurent Pouchain, Jean-Pierre Hurvois*, Claude Moinet
Laboratoire d’Electrochimie et Catalyse, UMR 6226, Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France
Fax: +33(2)23235967; e-Mail: Jean-Pierre.Hurvois@univ-rennes1.fr;

Abstract

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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 hydrogenolyzed to afforded (S)-(+)-coniine (99% ee) with an overall 35% yield from (-)-1-[(1S)-1-phenylethyl]piperidine.

Key words

alkaloids - anodic cyanation - alkylation - metallation - stereoselective synthesis

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References

References and Notes

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