Synthesis of 5-Vinyl-2-isoxazolines by Palladium-Catalyzed Intramolecular <i>O</i>-Allylation of Ketoximes
Rodney A. Fernandes, Ashvin J. Gangani, Arpita Panja
Abstract
An efficient method for the synthesis of 5-vinyl-2-isoxazolines by Pd-catalyzed intramolecular O-allylation of ketoximes has been developed. The reaction involves Pd(0)-catalyzed π-allyl formation via leaving group ionization or Pd(II)-catalyzed allylic C–H activation followed by intramolecular nucleophilic oxime oxygen attack. This methodology has been elaborated to various value-added products by epoxidation, Wacker oxidation, cross-metathesis, hydroboration–oxidation, dihydroxylation, and catalytic hydrogenation.
Topics & Concepts
ChemistryIntramolecular forceAllylic rearrangementCatalysisHydroborationNucleophileDihydroxylationPalladiumOximeMedicinal chemistryMetathesisWacker processOrganic chemistryEnantioselective synthesisPolymerizationPolymerSynthesis and Catalytic ReactionsChemical Synthesis and ReactionsCatalytic C–H Functionalization Methods