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Tetrabutylammonium Fluoride: A Powerful Catalyst for the Regioselective Opening of Epoxides with Thiols
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1994
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EngineeringOrganic ChemistryChemistryTetrabutylammonium FluorideOrganometallic CatalysisBiochemistryFluorous SynthesisO-protected GlycidolsCatalysisPowerful CatalystEnantioselective SynthesisCatalytic SynthesisBiomolecular EngineeringAlkene MetathesisNatural SciencesHigh RegioselectivityMolecular CatalysisRegioselective OpeningSynthetic Chemistry
Tetrabutylammonium fluoride (1) catalyses under mild conditions the opening of epoxides 2a-k with thiols 3-6 to produce the corresponding ß-hydroxy thioethers 7-11 in excellent yields (88-100%) and with high regioselectivity. Furthermore, O-protected glycidols react without any loss of the protective group.