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Asymmetric Catalysis with Chiral Phosphane/Phosphoramidite Ligands Derived from Quinoline (QUINAPHOS)
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2000
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EngineeringNatural SciencesDiversity-oriented SynthesisSelective LigandsOrganic ChemistryOrganometallic CatalysisCatalysisRh ComplexesChemistryChiral Quinaphos LigandsStereoselective SynthesisHomogeneous CatalysisAsymmetric CatalysisSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
Hydroformylation as well as hydrogenation are efficiently catalyzed by Rh complexes formed from chiral QUINAPHOS ligands (see picture), which are readily synthesized and are available in both enantiomeric forms. For example, (Ra,Rc)-nBu-QUINAPHOS (Ar=Ph, O−O=(Ra)-binaphthol, R=nBu) is among the most selective ligands known to date for the first reaction, and the (Ra,Sc) diastereomer forms extremely active (turnover frequency≥36 000 h−1) and highly selective (>99 % ee) Rh catalysts for the second reaction.