European Journal of Organic Chemistry · 2010 · 63 citations · 39 references
Natural SciencesChemical EngineeringChemistryCatalysisOrganic ChemistryOrganometallic ChemistryHeterocyclic ChemistryOrganic SynthesisCatalytic Reaction MechanismsEnantioselective CatalysisEnantioselective Catalyst DesignEnantioselective SynthesisLewis Acid CatalysisLewis AcidityMild Reaction ConditionsOrganocatalysis
Abstract A series of chiral organocatalysts and Lewis acids have been evaluated in the Lewis acid/organocatalysts‐based cooperative catalytic Biginelli reaction, which resulted in the determination of a novel cooperative Lewis acid/primary amine catalyst system, NbCl 5 /QN‐NH 2 . The synergistic effect of NbCl 5 and the quinine‐derived primary amine is pronounced and gave dihydropyrimidiones (DHPMs) in moderate to good enantioselectivities (up to 84 % ee ) and good to excellent yields (up to 99 % yield) under mild conditions.
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Bifunctional Asymmetric Catalysis: Cooperative Lewis Acid/Base Systems
Daniel H. Paull, Ciby J. Abraham, Michael T. Scerba et al. · Accounts of Chemical Research · 2008 · 370 citations · Full text