Organic Letters · 2008 · 30 citations · 34 references
Natural SciencesChemical EngineeringChemistryCatalysisOrganic ChemistryReaction EngineeringCatalyst DesignCatalyst PreparationCatalyst SynthesisCatalytic MaterialsCatalytic MechanismsCatalytic Reaction EngineeringBrønsted Acid CatalysisBrønsted AcidityCatalyst Development For SynthesisClaisen RearrangementHydrogen Bond Donor FeaturesPka Values
A bisamidinium catalyst has been designed for the Claisen rearrangement. The primary design feature is a dual hydrogen bonding array that can coordinate a singular oxygen atom of the substrate. The ability to function as a dual hydrogen donor is key as the bisamidinium accelerates the Claisen rearrangement to a greater extent than Brønsted acids with lower pK(a) values.
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