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....

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Bibliographic Details
Published in:Organic letters 2024-01, Vol.26 (3), p.692-696
Main Authors: Skibinska, Monika, Warowicka, Alicja, Koroniak, Henryk, Cytlak, Tomasz, Crousse, Benoît
Format: Article
Language:English
Subjects:
Chemical Sciences
Letter
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c04094