Enantioselective hydrogenation of N-acetyl dehydrophenylalanine methyl ester using cinchonine-modified Pd/TiO2 catalysts

N. J. Coulston, Richard Peter Kerwin Wells, P. B. Wells, G. J. Hutchings

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The enantioselective hydrogenation of N-acetyl dehydrophenylalanine methyl ester (NADPME) to N-acetyl phenylalanine methyl ester is investigated using cinchonine-modified Pd/TiO2 catalysts. The catalysts were prepared using deposition-reduction and wet impregnation methods and were evaluated for reaction using methanol as solvent with various cinchonine/NADPME molar ratios. Enantioselectivity was sensitive to this ratio and comparison with Pd/gamma-Al2O3 showed that the Pd/TiO2 gave marginally higher enantioselectivity when tested under comparable conditions. The effect of Pd loading and dispersion was investigated and the maximum enantiomeric excess observed was dependent on the dispersion: the role of the Pd particle size is discussed in the context of cinchonine adsorption. The reactions were carried out in solvents (methanol and dimethyl formamide) and mixed solvents (methanol-water and dimethyl formamide-water); the enantionteric excess was significantly enhanced using dimethyl formamide. The addition of water does not have a significant effect for the Pd/TiO2 catalysts. In this paper we report the highest enantiomeric excess for the hydrogenation of a prochiral ester using an iminobilised catalyst. (c) 2006 Elsevier B.V. All rights reserved.

Original languageEnglish
Pages (from-to)353-356
Number of pages3
JournalCatalysis Today
Volume114
DOIs
Publication statusPublished - 2006

Keywords

  • enantioselective hydrogenation
  • N-acetyl dehydrophenylalanine methyl ester
  • Pd/TiO2
  • cinchonine-modified Pd catalyst
  • MODIFIED PLATINUM
  • ASYMMETRIC HYDROGENATION
  • HETEROGENEOUS CATALYSIS
  • HOMOGENEOUS CATALYSTS
  • NICKEL-CATALYST
  • PYRUVATE
  • IMMOBILIZATION
  • RHODIUM
  • COMPLEXES
  • DESIGN

Cite this

Enantioselective hydrogenation of N-acetyl dehydrophenylalanine methyl ester using cinchonine-modified Pd/TiO2 catalysts. / Coulston, N. J.; Wells, Richard Peter Kerwin; Wells, P. B.; Hutchings, G. J.

In: Catalysis Today, Vol. 114, 2006, p. 353-356.

Research output: Contribution to journalArticle

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AU - Hutchings, G. J.

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AB - The enantioselective hydrogenation of N-acetyl dehydrophenylalanine methyl ester (NADPME) to N-acetyl phenylalanine methyl ester is investigated using cinchonine-modified Pd/TiO2 catalysts. The catalysts were prepared using deposition-reduction and wet impregnation methods and were evaluated for reaction using methanol as solvent with various cinchonine/NADPME molar ratios. Enantioselectivity was sensitive to this ratio and comparison with Pd/gamma-Al2O3 showed that the Pd/TiO2 gave marginally higher enantioselectivity when tested under comparable conditions. The effect of Pd loading and dispersion was investigated and the maximum enantiomeric excess observed was dependent on the dispersion: the role of the Pd particle size is discussed in the context of cinchonine adsorption. The reactions were carried out in solvents (methanol and dimethyl formamide) and mixed solvents (methanol-water and dimethyl formamide-water); the enantionteric excess was significantly enhanced using dimethyl formamide. The addition of water does not have a significant effect for the Pd/TiO2 catalysts. In this paper we report the highest enantiomeric excess for the hydrogenation of a prochiral ester using an iminobilised catalyst. (c) 2006 Elsevier B.V. All rights reserved.

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