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

Yang Yuan, Youcan Zhang and Xiao-Feng Wu ()
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Yang Yuan: Chinese Academy of Sciences
Youcan Zhang: Chinese Academy of Sciences
Xiao-Feng Wu: Chinese Academy of Sciences

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: 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.

Date: 2024
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DOI: 10.1038/s41467-024-51048-8

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