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Catalysed Asymmetric Protonation of Simple Linear Keto-Enolic Species − A Route to Chiral α-Arylpropionic Acids
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2002
Year
Asymmetric ProtonationEngineeringBiochemistryNatural SciencesEnolic SpeciesDiversity-oriented SynthesisA RouteActive α-Aryl Ketones2-Phenylpropionic AcidOrganic ChemistryChemistryNatural Product SynthesisAsymmetric CatalysisSynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringChiral α-Arylpropionic Acids
The reaction cascade consisting of deprotection/decarboxylation/asymmetric protonation of enolic species, starting from open-chain benzyl β-oxo esters, has been studied. When carried out in the presence of catalytic amounts of cinchonine, the reaction gave optically active α-aryl ketones with up to 75% ee. Enantio-enriched (S)-3-phenyl-2-butanone can be converted into 2-phenylpropionic acid without racemisation. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)