Organic Letters · 2010 · 136 citations · 29 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryCatalyst SynthesisCatalytic MechanismsHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsOrganic SynthesisC - H Bond FunctionalizationCatalytic Reaction MechanismsHeterocycle FunctionalizationHeterocyclic ReactivityLewis Acid CatalysisSubstituent Effects In Pyranoses
An expeditious construction of a benzopyran skeleton via Lewis acid-catalyzed C-H functionalization was achieved. In this process, a [1,5] hydride shift and 6-endo cyclization successively occurred to give benzopyrans. The presence of substituents ortho to the alkoxy group significantly enhanced the reactivity, affording the desired compounds in excellent chemical yields with short reaction times.
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C-H Bond Functionalization in Complex Organic Synthesis
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