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A Versatile Palladium-Mediated Three-Component Reaction for the One-Pot Synthesis of Stereodefined 3-Arylidene-(or 3-Alkenylidene-)tetrahydrofurans

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journal contribution
posted on 14.12.2000, 00:00 by Marilyn Bottex, Marcello Cavicchioli, Benoît Hartmann, Nuno Monteiro, Geneviève Balme
A one-pot reaction between equimolecular amounts of various propargyl alcohols, Michael acceptors, and unsaturated halides (or triflates) in the presence of a palladium(0) catalyst provides a simple and flexible entry into highly substituted 3-arylidene-(or 3-alkenylidene-)tetrahydrofurans. The efficiency of this palladium-mediated three-component reaction has been shown to be strongly influenced by the nature of the catalyst system, and in this regard, a palladium(0) catalyst generated in situ by reduction of PdCl2(PPh3)2 with n-butyllithium has been found particularly effective.