Synthesis of the (α,α-difluoroalkyl)phosphonate analogue of phosphoserine

Article abstract of DOI:10.1016/S0040-4039(00)78242-6

The synthesis of the (α,α-difluoroalkyl)phosphonate analogue of L- phosphoserine, 5, in a form appropriate for solid phase peptide synthesis, is reported. Two independent routes are described, starting from L-serine or (R)-isopropylideneglycerol. In each case, PCF₂-C bond formation is achieved by triflate displacement with diethyl lithiodifluoromethylphosphonate.