Photoredox-Catalyzed Difluoromethylation of Dehydroalanine and Dehydroalanine-Containing Dipeptides: A Proof-of-Concept Enantioselective Variant
Yue Zhang, Hangzhi Jiang, Shengqun Zhang, Yiqian Li, Tianshuai Zhu, Guangwei Wu, Jing-Jing Zhang, Xingfeng Bai, Zhen Chen
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Source: Crossref
Published: Oct 2, 2026
DOI: 10.1021/acs.orglett.6c03908
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Abstract A photoredox-catalyzed difluoromethylation of dehydroalanine (Dha) derivatives and protected Dha-containing dipeptides is described. The reaction enables direct installation of the CF2H group to access β-difluoromethyl α-amino acid derivatives under mild conditions using difluoromethyl sulfone as the radical precursor. A proof-of-concept CPA-enabled enantioselective variant furnished the model product in 55% isolated yield and 73% ee. Mechanistic experiments support a radical–polar crossover pathway and suggest that reversible product deprotonation may contribute to stereochemical erosion.
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