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Note | Regular issue | Vol 48, No. 10, 1998, pp.2157-2162
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8274
Unexpected Enolization of 2-Phenyl-3-piperidone Derivatives

Valérie Daley, Christian Cavé,* and Jean d'Angelo*

*Unité de Chimie Organique Associé au CNRS, Centre d'Etudes Pharmaceutiques, Université de Paris-Sud, 5, rue Jean-Baptiste Clément, 92296 Chatenay-Malabry Cedex, France

Abstract

Alkylation of 2-phenyl-3-piperidone (17) with methyl iodide or methyl acrylate furnished the 4,4-dialkylated derivatives (18) or (19), respectively. This unexpected enolization towards the less substituted form can be interpreted considering the appreciable steric strain which would exist in the more substituted enolate (21).