title: Efficient synthesis of fluorophosphonylated alkyles by ring-opening reaction of cyclic sulfates.
abstract: Ring-opening reactions of functionalized 1,2-cyclic sulfates and oxetanes with the phosphonodifluoromethyl carbanion are reported. This approach allows an easy access to fluorinated beta-hydroxyphosphonates that are building blocks in the synthesis of acyclic nucleosides. Synthesis of precursors of nucleoside phosphorylase inhibitors from these alcohols is described.
authors.affiliation: Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, UMR-CNRS 6507, 6 Bd du Maréchal Juin, 14050 Caen Cedex, France.
authors.forename: Sonia Amel
authors.initials: SA
authors.lastname: Diab
authors.forename: Aboubacary
authors.initials: A
authors.lastname: Sene
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Pfund
authors.forename: Thierry
authors.initials: T
authors.lastname: Lequeux
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D000478:Alkylation; D004988:Ethers, Cyclic / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000737:chemistry; D063065:Organophosphonates / Q000138:chemical synthesis*; D013463:Sulfuric Acid Esters / Q000737:chemistry*
chemical_list: D000438:Alcohols; D004988:Ethers, Cyclic; D006845:Hydrocarbons, Fluorinated; D063065:Organophosphonates; D013463:Sulfuric Acid Esters; C005287:oxetane