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<p>γ-Amino acids have received increasing attention due to their biological activity in natural products and pharmaceuticals. Meanwhile, indole derivatives represent a class of privileged compounds in biological, medicinal, and organic chemistry, with new approaches to their functionalization in demand. A general method for the union of indole and γ-amino acid pharmacophores, however, has not been realized. Herein, we report a novel copper-catalyzed radical dicarbofunctionalization of 2-azadienes with α-bromo carbonyl compounds and indoles. This cascade reaction generates two new C–C bonds in a single step through an intermolecular three-component coupling, providing a wide array of γ-amino acids containing C3-substituted indole units with complete chemo- and regioselectivity (41 examples, 50%–90% yields). This transformation can also be used to elaborate natural products and drug molecules. Mechanistic studies indicate α-carbonyl and 2-azaallyl radicals in a copper-mediated coupling process.</p>

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Copper-catalyzed synthesis of γ-amino acids with indole units via radical dicarbofunctionalization of 2-azadienes

  • 期刊论文

  • 发表日期：

    2026年3月19日

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  • Shengzu Duan,
  • Ya Du,
  • Lening Zhang,
  • Shuntao Huang,
  • Sina Liu,
  • Xiang Yang,
  • Hongbin Zhang,
  • Patrick J. Walsh,
  • Xiaodong Yang

摘要

γ-Amino acids have received increasing attention due to their biological activity in natural products and pharmaceuticals. Meanwhile, indole derivatives represent a class of privileged compounds in biological, medicinal, and organic chemistry, with new approaches to their functionalization in demand. A general method for the union of indole and γ-amino acid pharmacophores, however, has not been realized. Herein, we report a novel copper-catalyzed radical dicarbofunctionalization of 2-azadienes with α-bromo carbonyl compounds and indoles. This cascade reaction generates two new C–C bonds in a single step through an intermolecular three-component coupling, providing a wide array of γ-amino acids containing C3-substituted indole units with complete chemo- and regioselectivity (41 examples, 50%–90% yields). This transformation can also be used to elaborate natural products and drug molecules. Mechanistic studies indicate α-carbonyl and 2-azaallyl radicals in a copper-mediated coupling process.