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Electrophilic Heteroatom Cyclization of w-Alkenylphoshonic Acid Half Esters Giving Cyclic Phosphonates (Phostones)
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1997
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Enantioselective SynthesisEngineeringHeterocyclicAlkene MetathesisReductive DeselenenylationOrganic ChemistrySequential Seleno-pummerer RearrangementSynthetic ChemistryStereoselective SynthesisChemistryHeterocycle ChemistryElectrophilic Heteroatom CyclizationElectrophilic Heteroatom CyclizationsBiomolecular Engineering
Electrophilic heteroatom cyclizations of walkenylphosphonic acid half esters (4a-d) with NBS orphenylselenenyl chloride were examined to give the cyclic phosphonates (phostones) (6a-d and 7a-d).The phenyselenomethylphostone (7c) was converted to the acetoxymethylphostone (9) through sequential seleno-Pummerer rearrangement and reductive deselenenylation.