Copper/Palladium-Catalyzed 1,4 Reduction and Asymmetric Allylic Alkylation of α,β-Unsaturated Ketones: Enantioselective Dual Catalysis

Authors

  • Fady Nahra,

    1. Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST)—Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.03, 1348 Louvain-la-Neuve (Belgium)
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  • Dr. Yohan Macé,

    1. Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST)—Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.03, 1348 Louvain-la-Neuve (Belgium)
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  • Dr. Dominique Lambin,

    1. Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST)—Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.03, 1348 Louvain-la-Neuve (Belgium)
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  • Prof. Olivier Riant

    Corresponding author
    1. Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST)—Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.03, 1348 Louvain-la-Neuve (Belgium)
    • Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST)—Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.03, 1348 Louvain-la-Neuve (Belgium)

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  • Financial support from the Université Catholique de Louvain, FNRS, and Région Bruxelloise is gratefully acknowledged.

Abstract

original image

Cooperative efforts: The catalytic coupling of the two organometallic intermediates is possible through a Cu/Pd-based dual catalysis (see scheme; LG=leaving group), in which the CuI catalytic cycle generates catalytically the starting material for the Pd0 catalytic cycle. Although reagents are present in stoichiometric amounts in the reaction mixture and are able to trap both active species, the desired reaction proceeds as planned.

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