Asymmetric Hydrogenation of α-Acetamidocinnamic Acid with Chiral Rhodium Complexes of DIOP and BPPM on Charcoal

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Chiral rhodium (I) complexes of (-)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis (diphenylphosphino) butane (DIOP) and (2S, 4S) -N-butoxycarbonyl-4-diphenylphosphino-2-diphenyl-phosphinomethylpyrrolidine (BPPM) were fixed on charcoal which had been pretreated with metal acetates and triethylamine, and the hydrogenation of α-acetamidocinnamic acid was performed in an ethanol-H_2O (1 : 1) mixture. L-N-Acetyl- (R) -phenylalanine was obtained in optical yields of 70.5% with RhCl (COD) -DIOP-charcoal catalyst and 86.5% with RhCl (COD) -BPPM-charcoal catalyst. The optical yields were affected by hydrogen pressure, reaction temperature, the concentration of the substrate, and the composition of the solvent. The recovered catalyst retained its activity well and could be re-used repeatedly for enantioface-differentiating hydrogenation, provided that it was kept under a nitrogen atmosphere throughout.
公益社団法人日本薬学会の論文
1983-10-25