Synthesis and spectral properties of fluorinated α,β-epoxyphosphonates

Abstract The methods of synthesis of two type of monofluorinated α , β -epoxyphosphonates, fosfomycin analogues, with the vicinal and geminal arrangement of fluorine and phosphorus atoms have been developed. The electrophilic monofluorination of enamine or β -enaminophosphonate using Selectfluor ® have been evaluated. The selective bromination of resulting α -fluoro ketone followed by addition of phosphite and cyclization gave first desired α , β -epoxyphosphonate. The α -fluoro- β -ketophosphonate has been converted into various fluorinated haloalcohols via halogenation and reduction with borane complex. The reaction of ring closure of fluorohalohydrin has yielded oxirane or appropriate phosphates. The products structure has been confirmed by 1 H, 13 C, 19 F and 31 P NMR spectroscopy.