Work

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

Year: 2025

Type: article

Abstract: 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. Chiral γ-butenolides, which are widely prevalent in natural products and pharmaceuticals, necessitate synthetic methods that precisely control both stereochemistry and substituent diversity. Here, the authors report a Cu/PyBim-catalyzed asymmetric lactonization of 2,3-allenoic acids initiated by sulfonyl or phosphonyl radicals.

Source: Nature Communications

DOI: 10.1038/s41467-025-64398-8

Authors: Bingxu Han, Zaicheng Nie, Changqing Ye, Hongli Bao

Institutions: Chinese Academy of Sciences, Fujian Institute of Research on the Structure of Matter, State Key Laboratory of Structural Chemistry, Fuzhou University, University of Chinese Academy of Sciences

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $6,990

Funders: National Natural Science Foundation of China, Chinese Academy of Sciences, Natural Science Foundation of Fujian Province