Organic Letters · 2010 · 142 citations · 63 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryDiversity-oriented SynthesisHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsOrganic SynthesisRetrosynthetic AnalysisAromatic HeterocyclesAza-claisen RearrangementClaisen RearrangementDirect SynthesisDiversity-oriented Heterocycle SynthesisIsoxazole ChemistryIsoxazole SynthesisTransition-metal-catalyzed Heterocycle Synthesis
Alkynyl oxime ether underwent a gold-catalyzed domino reaction involving cyclization and subsequent Claisen-type rearrangement to afford trisubstituted isoxazoles in a direct, efficient, and regioselective manner. The products were successfully applied to the synthesis of unusual heterocycles as an illustration of the potential utility of the reaction.
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