The Journal of Organic Chemistry · 2013 · 77 citations · 48 references
Cross-coupling ReactionWacker-type OxidationEngineeringAlkene MetathesisOxidation ResistanceCatalytic SynthesisTotal SynthesisOrganic ChemistryCatalysisInternal AlkenesChemistryHeterocycle ChemistryPharmacologyAdvanced IntermediateSynthetic ChemistryBiomolecular Engineering
The Pd-catalyzed TBHP-mediated Wacker-type oxidation of internal alkenes is reported. The reaction uses 2-(4,5-dihydro-2-oxazolyl)quinoline (Quinox) as ligand and TBHP(aq) as oxidant to deliver single ketone constitutional isomer products in a predictable fashion from electronically biased olefins. This methodology is showcased through its application on an advanced intermediate in the total synthesis of the antimalarial drug artemisinin.
48