Highly Diastereo- and Enantioselective Copper-Catalyzed Domino Reduction/Aldol Reaction of Ketones with Methyl Acrylate

Authors

  • Julia Deschamp,

    1. Unité de chimie organique et médicinale Université catholique de Louvain, Place Louis Pasteur 1, 1348 Louvain-la-Neuve, Belgium, Fax: (+32) 1047-4168
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  • Olivier Chuzel,

    1. Unité de chimie organique et médicinale Université catholique de Louvain, Place Louis Pasteur 1, 1348 Louvain-la-Neuve, Belgium, Fax: (+32) 1047-4168
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  • Jérôme Hannedouche Dr.,

    1. Unité de chimie organique et médicinale Université catholique de Louvain, Place Louis Pasteur 1, 1348 Louvain-la-Neuve, Belgium, Fax: (+32) 1047-4168
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  • Olivier Riant Prof.

    1. Unité de chimie organique et médicinale Université catholique de Louvain, Place Louis Pasteur 1, 1348 Louvain-la-Neuve, Belgium, Fax: (+32) 1047-4168
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  • This work was supported by the Université Catholique de Louvain. Dr. B. Pugin (Solvias) and Dr. R. Schmid (Hoffmann–La Roche) are gratefully acknowledged for generous gifts of chiral ligands. Mr. V. Van Tran is also acknowledged for his assistance with the chiral analysis of the new compounds.

Abstract

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A good choice: A new catalytic method was found for the construction of stereogenic quaternary carbon centers through a copper-catalyzed domino conjugated reduction/aldol reaction of methyl acrylate with various alkyl aryl ketones. The proper choice of the chiral diphosphine ligand leads to high chemo-, diastereo-, and enantioselectivity.

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