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Catalytic Enantioselective Reduction of β,β-Disubstituted Vinyl Phenyl Sulfones by Using Bisphosphine Monoxide Ligands

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  • This work was supported by NSERC (Canada), Merck Frosst Canada Ltd., Boehringer Ingelheim (Canada) Ltd., the Canada Research Chairs Program, the Canadian Foundation for Innovation, and the Université de Montréal. J.-N.D. is grateful to NSERC (CGS D) for a postgraduate fellowship.

Abstract

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Synthesis of chiral sulfones: A copper–phosphine complex efficiently provided optically active alkyl phenyl sulfones by hydrosilylation at room temperature. The reduction of β,β-disubstituted vinyl sulfones in the presence of the Me-DuPhos monoxide ligand lead to excellent enantiomeric excesses and high yields (see scheme). The prepared chiral sulfones were desulfonylated and subjected to Julia olefination conditions.

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