Efficient Synthesis of Fluorophosphonylated Alkyles by Ring-Opening Reaction of Cyclic Sulfates

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 β-hydroxyphosphonates that are building blocks in the synthesis of acyclic nucleosides. Synthesis of precursors of nuc...

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Bibliographic Details
Published in:Organic letters 2008-09, Vol.10 (17), p.3895-3898
Main Authors: Diab, Sonia Amel, Sene, Aboubacary, Pfund, Emmanuel, Lequeux, Thierry
Format: Article
Language:English
Subjects:
Alcohols - chemical synthesis
Alcohols - chemistry
Alkylation
Ethers, Cyclic - chemistry
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Organophosphonates - chemical synthesis
Sulfuric Acid Esters - chemistry
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Summary: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 β-hydroxyphosphonates that are building blocks in the synthesis of acyclic nucleosides. Synthesis of precursors of nucleoside phosphorylase inhibitors from these alcohols is described.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol801443s