The Journal of Organic Chemistry · 2005 · 33 citations · 36 references
Natural SciencesChemical EngineeringChemistryCatalysisOrganic ChemistryOrganometallic ChemistryCatalyst DesignCatalyst PreparationCatalyst SynthesisCatalytic MaterialsChiral SeparationOrganic SynthesisAlkylation CatalysisAsymmetric CatalysisAsymmetric Catalyst DesignAsymmetric SynthesisEnantioselective Catalyst DesignEnantioselective SynthesisLigand SelectivityPalladium Catalysts
[Chemical reaction: See text] Chiral fluorous aminophosphine 4c bearing two fluorous ponytails was prepared from (S)-prolinol and applied to palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate (7) with a dialkyl malonate-BSA-LiOAc system with high enantioselectivities (up to 97% ee). Results indicated that the chiral fluorous palladium catalyst from ligand 4c was easily separated from the reaction mixture by simple solid/liquid separation and could be reused up to five times.
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