Syntheses of omega-hydroxy-alpha,alpha-difluoromethylphosphonates by oxacycle ring-opening reactions.

Oxacycle ring-opening reactions from a non-HCFC-based source of phosphonodifluoromethyl carbanion 1 are reported. This straightforward strategy opens access to a variety of primary and secondary omega-hydroxy-alpha,alpha-difluoromethylphosphonates via one step. The syntheses of a glycerol monophosphate analogue and precursors to nucleoside phosphorylase inhibitors are described using this method.