Synthesis, Reactivity, and Antibacterial Activity of gem-Difluoroalkene, Difluoromethyl, and Trifluoromethyl β-Lactams.

New gem-difluoroalkenes were synthesized by the dehydrofluorination of the corresponding 4-CF3-β-lactams. An unexpected rearrangement mechanism of the ester moiety dependent on a stabilizing negative charge was observed. Hydrogenation to 4-CHF2-β-lactams was successful from gem-difluoro-β-lactams.

Citation

Monika Skibinska, Alicja Warowicka, Henryk Koroniak, Tomasz Cytlak, Benoît Crousse. Synthesis, Reactivity, and Antibacterial Activity of gem-Difluoroalkene, Difluoromethyl, and Trifluoromethyl β-Lactams. Organic letters. 2024 Jan 26;26(3):692-696

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PMID: 38227548

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