Syntheses of omega-hydroxy-alpha,alpha-difluoromethylphosphonates by oxacycle ring-opening reactions.
[reaction: see text] 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.
Ozouf
Paul
P
Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, ENSICAEN Université de Caen, 6 Boulevard du Maréchal Juin, 14050 Caen, France.
Binot
Grégory
G
Pommelet
Jean-Claude
JC
Lequeux
Thierry P
TP