Copper-Catalyzed Addition of Nucleophilic Silicon to Aldehydes

Authors

  • Virginie Cirriez,

    1. Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST)—Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve (Belgium)
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  • Corentin Rasson,

    1. Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST)—Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve (Belgium)
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  • Thomas Hermant,

    1. Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST)—Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve (Belgium)
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  • Dr. Julien Petrignet,

    1. Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST)—Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve (Belgium)
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  • Dr. Jesús Díaz Álvarez,

    1. Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST)—Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve (Belgium)
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  • Dr. Koen Robeyns,

    1. Institute of Condensed Matter and Nanosciences, Molecules, Solids and Reactivity (IMCN/MOST)—Université Catholique de Louvain, Place Louis Pasteur 1, bte L4.01.02, 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 L4.01.02, 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 L4.01.02, 1348 Louvain-la-Neuve (Belgium)
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  • Financial support from the Université Catholique de Louvain is gratefully acknowledged. Takasago International is gratefully acknowledged for a generous gift of Segphos ligands. Laurent Collard is gratefully acknowledged for his work on the separation of chiral products.

Abstract

original image

How to train your silane: A new family of chiral copper(I) complexes that bear a bifluoride counteranion were prepared and used in the first example of the enantioselective transfer of a silyl group to an aldehyde. This procedure provides fast access to non-racemic α-hydroxysilanes in high enantioselectivities.

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