Enantioselective hydrogenation of α-keto esters over cinchona-Pt/Al2O3 catalyst. Kinetic evidence for the substrate-modifier interaction in the liquid phase

József L. Margitfalvi, M. Hegedűs, E. Tfirst

Research output: Contribution to journalArticle

72 Citations (Scopus)

Abstract

The hydrogenation of ethyl pyruvate was studied over cinchonidine-Pt/Al2O3 catalyst. Contrary to earlier results it has been found that the initial enantiomeric excess extrapolated to zero conversion is close to zero. Based on kinetic analysis the results are considered as indirect evidence for the substrate-modifier interaction taking place in the liquid phase. The above interaction leads to the formation of a weak substrate-modifier complex. The formation of the complex in the liquid phase is the key step to control both the rate acceleration and the induction of enantio-differentiation in the hydrogenation of α-keto esters in the presence of cinchona-Pt/Al2O3 catalysts. The character of interactions in the substrate-modifier complex is discussed. By using molecular modelling the possible form of the complex is also given.

Original languageEnglish
Pages (from-to)571-580
Number of pages10
JournalTetrahedron Asymmetry
Volume7
Issue number2
DOIs
Publication statusPublished - Feb 1996

Fingerprint

Cinchona
Hydrogenation
hydrogenation
esters
Esters
liquid phases
catalysts
Catalysts
Kinetics
kinetics
Liquids
Substrates
pyruvates
Molecular modeling
interactions
induction

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

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title = "Enantioselective hydrogenation of α-keto esters over cinchona-Pt/Al2O3 catalyst. Kinetic evidence for the substrate-modifier interaction in the liquid phase",
abstract = "The hydrogenation of ethyl pyruvate was studied over cinchonidine-Pt/Al2O3 catalyst. Contrary to earlier results it has been found that the initial enantiomeric excess extrapolated to zero conversion is close to zero. Based on kinetic analysis the results are considered as indirect evidence for the substrate-modifier interaction taking place in the liquid phase. The above interaction leads to the formation of a weak substrate-modifier complex. The formation of the complex in the liquid phase is the key step to control both the rate acceleration and the induction of enantio-differentiation in the hydrogenation of α-keto esters in the presence of cinchona-Pt/Al2O3 catalysts. The character of interactions in the substrate-modifier complex is discussed. By using molecular modelling the possible form of the complex is also given.",
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T1 - Enantioselective hydrogenation of α-keto esters over cinchona-Pt/Al2O3 catalyst. Kinetic evidence for the substrate-modifier interaction in the liquid phase

AU - Margitfalvi, József L.

AU - Hegedűs, M.

AU - Tfirst, E.

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N2 - The hydrogenation of ethyl pyruvate was studied over cinchonidine-Pt/Al2O3 catalyst. Contrary to earlier results it has been found that the initial enantiomeric excess extrapolated to zero conversion is close to zero. Based on kinetic analysis the results are considered as indirect evidence for the substrate-modifier interaction taking place in the liquid phase. The above interaction leads to the formation of a weak substrate-modifier complex. The formation of the complex in the liquid phase is the key step to control both the rate acceleration and the induction of enantio-differentiation in the hydrogenation of α-keto esters in the presence of cinchona-Pt/Al2O3 catalysts. The character of interactions in the substrate-modifier complex is discussed. By using molecular modelling the possible form of the complex is also given.

AB - The hydrogenation of ethyl pyruvate was studied over cinchonidine-Pt/Al2O3 catalyst. Contrary to earlier results it has been found that the initial enantiomeric excess extrapolated to zero conversion is close to zero. Based on kinetic analysis the results are considered as indirect evidence for the substrate-modifier interaction taking place in the liquid phase. The above interaction leads to the formation of a weak substrate-modifier complex. The formation of the complex in the liquid phase is the key step to control both the rate acceleration and the induction of enantio-differentiation in the hydrogenation of α-keto esters in the presence of cinchona-Pt/Al2O3 catalysts. The character of interactions in the substrate-modifier complex is discussed. By using molecular modelling the possible form of the complex is also given.

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