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<p>Chiral γ-butenolides, which are widely prevalent in natural products and pharmaceuticals, necessitate synthetic methods that precisely control both stereochemistry and substituent diversity. In this study, we report a Cu/PyBim-catalyzed asymmetric lactonization of 2,3-allenoic acids initiated by sulfonyl or phosphonyl radicals. This strategy facilitates the direct construction of enantioenriched γ-butenolides featuring modular endocyclic double bond substituents, thereby circumventing the traditional reliance on prefunctionalized substrates. Synthetic applications of the obtained chiral γ-butenolide are emphasized and mechanistic experiments are investigated.</p>

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Copper-catalyzed enantioselective synthesis of γ-butenolides via radical diversification of allenoic acid

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年10月23日

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  • Bingxu Han,
  • Zaicheng Nie,
  • Changqing Ye,
  • Hongli Bao

摘要

Chiral γ-butenolides, which are widely prevalent in natural products and pharmaceuticals, necessitate synthetic methods that precisely control both stereochemistry and substituent diversity. In this study, we report a Cu/PyBim-catalyzed asymmetric lactonization of 2,3-allenoic acids initiated by sulfonyl or phosphonyl radicals. This strategy facilitates the direct construction of enantioenriched γ-butenolides featuring modular endocyclic double bond substituents, thereby circumventing the traditional reliance on prefunctionalized substrates. Synthetic applications of the obtained chiral γ-butenolide are emphasized and mechanistic experiments are investigated.