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Efficient Asymmetric Hydrogenation of .BETA.- and .GAMMA.-Amino Ketone Derivatives Leading to Practical Synthesis of Fluoxetine and Eprozinol.
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1995
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EngineeringOrganic ChemistryChemistryActive Amino AlcoholsMedicinal ChemistryPractical SynthesisAsymmetric HydrogenationsEfficient Asymmetric HydrogenationStereoselective SynthesisDerivatives.Gamma.-amino Ketone DerivativesBiochemistryDiversity-oriented SynthesisCatalysisAsymmetric CatalysisEnantioselective SynthesisBiomolecular EngineeringNatural SciencesEfficient Syntheses
N-(Methylcarbamoyl)-4-(dicyclohexylphosphino)-2-[(diphenylphosphino)methyl]pyrrolidine (MCCPM)- and N-(tert-butoxycarbonyl)-4-(dicyclohexylphosphino)-2-[(diphenylphosphino)methyl]pyrrolidine (BCPM)-rhodium(I) complexes werer efficient catalysts for asymmetric hydrogenations of β- and γ-amino ketone hydrochloride derivatives. Utilizing this methodology, we have developed efficient syntheses of fluoxetine and eprozinol from intermediate optically active amino alcohols.