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Enantiospecific Synthesis of Pyridinones as Versatile Intermediates toward Asymmetric Piperidines

Nicolas Gouault*, Myriam Le Roch, Adèle Cheignon, Philippe Uriac and Michèle David

*Equipe Produits Naturels, Synthèse et Chimie Médicinale, UMR 6226 Sciences Chimiques de Rennes, Université de Rennes 1, 2 Avenue du Pr Léon Bernard 35043 Rennes Cedex, France, Email: nicolas.gouaultuniv-rennes1.fr

N. Gouault, M. Le Roch, A. Cheignon, P. Uriac, M. David, Org. Lett., 2011, 13, 4371-4373.

DOI: 10.1021/ol201698m



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Abstract

An enantiospecific syntheses of pyridinones from amino acids via a gold-catalyzed strategy allows excellent stereocontrol during cyclization. This approach provides a straightforward tool for further synthetic applications toward piperidines.

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Gold-Mediated Synthesis and Functionalization of Chiral Halopyridones

K. H. Nguyen, S. Tomasi, M. Le Roch, L. Toupet, J. Renault, P. Uriac, N. Gouault, J. Org. Chem., 2013, 78, 7809-7815.


Key Words

2,3-dihydro-4-pyridones


ID: J54-Y2011-2330