FeCl₃-Catalyzed Highly Diastereoselective Synthesis of Substituted Piperidines and Tetrahydropyrans

Amandine Guérinot, Anna Serra-Muns, Christian Gnamm, Charlélie Bensoussan, Sébastien Reymond* and Janine Cossy*

*ESPCI ParisTech, Laboratoire de Chimie Organique, UMR CNRS 7084, 10, Rue Vauquelin, 75231 Paris Cedex 05, France, Email: sebastien.reymondespci.fr, janine.cossyespci.fr

A. Guérinot, A. Serra-Muns, C. Gnamm, C. Bensoussan, S. Reymond, J. Cossy, Org. Lett., 2010, 12, 1808-1811.

DOI: 10.1021/ol100422d

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Abstract

Key step of an eco-friendly and highly diastereoselective synthesis of substituted cis-2,6-piperidines and cis-2,6-tetrahydropyrans is an iron-catalyzed thermodynamic equilibration of 2-alkenyl 6-substituted piperidines and 2-alkenyl 6-substituted tetrahydropyrans allowing the isolation of enriched mixtures of the most stable cis-isomers.

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Key Words

piperidines, tetrahydropyrans

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ID: J54-Y2010-1110