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Cyclizations of γ-Hydroxyallenes Mediated by Organopalladium Halides: A Convergent Synthetic Route to Substituted 5-Alkenyl-2-furanones and 2-Alkenyltetrahydrofurans
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References
1993
Year
4,5-Hexadienoic AcidEngineeringHeterocyclicSubstituted 5-Alkenyl-2-furanonesVarious β-AllenylcarbinolsAlkene MetathesisConvergent Synthetic RouteOrganic ChemistryOrganopalladium HalidesCatalysisChemistryHeterocycle ChemistryIntramolecular OxypalladationPharmacologyEnantioselective SynthesisBiomolecular Engineering
When a γ-hydroxyallene (various β-allenylcarbinols or 4,5-hexadienoic acid) is allowed to react with aryl or alkenyl halides in the presence of (Ph3P)4Pd and base, cyclization and coupling to form the title compounds in 14 - 78 (average 50)% yields occurs. A mechanism in which an aryl- or alkenylpalladium(II) halide initiates the cyclization by intramolecular oxypalladation is discussed.