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A simple route to side-chain fluorinated β-lactams from ring-fluorinated aziridines |
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| Authors: | Alexander S Konev Alexander F Khlebnikov Kourosch Abbaspour Tehrani |
| Institution: | a Department of Chemistry, St. Petersburg State University, Universitetskii pr. 26, 198504 St. Petersburg, Petrodvorets, Russia b Faculty of Science, Department of Applied Biological Sciences, Laboratory for Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium |
| Abstract: | β-Lactams bearing a Ph2CF substituent at the C(4)-atom were synthesized from N-alkyl-2-fluoro-3,3-diphenylaziridines. The transformation was realized using SbF3-mediated isomerization of the monofluoroaziridines to fluorinated aldimines, followed by Staudinger reaction with ketenes. It was shown that this reaction sequence can be performed as a one-pot procedure. |
| Keywords: | Fluoroaziridines Fluorinated aldimines Fluorine-containing β-lactams |
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