Catalytic Enone Cycloallylation via Concomitant Activation of Latent Nucleophilic and Electrophilic Partners: Merging Organic and Transition Metal Catalysis

Bradley G. Jellerichs, Jong-Rock Kong and Michael J. Krische*

*University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, Email: mkrischemail.utexas.edu

B. G. Jellerich, J.-R. Kong, M. J. Krische, J. Am. Chem. Soc., 2003, 125, 7758-7759.

DOI: 10.1021/ja0301469

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Abstract

An efficient cycloallylation of mono-enone mono-allylic carbonates is achieved upon exposure to tributylphosphine and 1 mol % Pd(Ph₃P)₄. This transformation combines the nucleophilic features of the Morita-Baylis-Hillman reaction with the electrophilic features of the Trost-Tsuji reaction.

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proposed mechanism

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Key Words

Enones, Tsuji-Trost Reaction, Cylcopentens, Cyclohexenes

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ID: J48-Y2003-1500