Highly efficient methods for the one-pot synthesis of β-substituted enones

William J. Kerr*, Colin M. Pearson and Graeme J. Thurston

*WestCHEM, Department of Pure and Applied Chemistry, University of Strathcycle, 295 Cathedral Street, Glasgow, Scotland, UK G1 1XL, Email: w.kerrstrath.ac.uk

W. J. Kerr, C. M. Person, G. J. Thurston, Org. Biomol. Chem., 2006, 4, 47-50.

DOI: 10.1039/b512177a

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Abstract

A mild and practically-convenient one-pot procedure for the direct β-substitution of enones has been developed using a conjugate addition-oxidation strategy with a full range of copper-based reagents (R₂CuLi, RCu.SMe, RCu, R(2-thienyl)Cu(CN)Li₂) and N-tert-butylphenylsulfinimidoyl chloride. Cyclic and acyclic, alkyl- and aryl-substituted enones are delivered in good to excellent yields.

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proposed mechanism

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Key Words

Substituted Enones

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ID: J52-Y2006-020