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Enantioselective synthesis of γ-chiral amides via copper-catalyzed reductive relay hydroaminocarbonylation

Author

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  • Yang Yuan

    (Chinese Academy of Sciences)

  • Youcan Zhang

    (Chinese Academy of Sciences
    Shanghai University of Engineering Science)

  • Xiao-Feng Wu

    (Chinese Academy of Sciences
    Leibniz-Institut für Katalyse e.V.)

Abstract

Chiral amides are common and effective structural motifs found in many pharmaceuticals and biologically active molecules. Despite their importance, existing synthetic methods are predominantly employed for the synthesis of α-amides and β-amides. The synthesis of remote chiral amides, characterized by distal stereocenters, typically requires intricate synthetic steps conducted under demanding conditions. Here, we present a general procedure for the copper-catalyzed enantioselective synthesis of γ-chiral amides, employing a reductive relay hydroaminocarbonylation strategy with trisubstituted allylic benzoates and hydroxylamine electrophiles. This approach demonstrates a wide substrate scope with excellent enantioselectivity and regioselectivity, thus providing access to challenging enantioenriched γ-chiral amides.

Suggested Citation

  • Yang Yuan & Youcan Zhang & Xiao-Feng Wu, 2024. "Enantioselective synthesis of γ-chiral amides via copper-catalyzed reductive relay hydroaminocarbonylation," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
  • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-51048-8
    DOI: 10.1038/s41467-024-51048-8
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    References listed on IDEAS

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    1. Tian-Sheng Mei & Harshkumar H. Patel & Matthew S. Sigman, 2014. "Enantioselective construction of remote quaternary stereocentres," Nature, Nature, vol. 508(7496), pages 340-344, April.
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