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Synlett 2007(10): 1613-1615  
DOI: 10.1055/s-2007-982547
LETTER
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of 2-Monosubstituted and 2,6-Disubstituted Piperidines

Isabelle Abrunhosa-Thomas, Olivier Roy, Marielle Barra, Tatiana Besset, Pierre Chalard*, Yves Troin*
Laboratoire de Chimie des Hétérocycles et des Glucides, EA 987, Ecole Nationale Supérieure de Chimie de Clermont-Ferrand, Université Blaise Pascal, BP 187, 63174 Aubière Cedex, France
Fax: +33(4)73407008; e-Mail: Yves.Troin@chimie.univ-bpclermont.fr;
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Publication History

Received 15 March 2007
Publication Date:
06 June 2007 (online)

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Abstract

An intramolecular Michael-type reaction, involving β′-amino-α,β-unsaturated ketone is used to prepare 2-mono- and 2,6-disusbtituted piperidines in a diastereoselective manner. This ­strategy allows an easy access to 2,6-trans-piperidine, starting from either E- or Z-olefin configuration.

Key words

piperidines - intramolecular Michael reaction - diaste­reoselectivity

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