Enantioselective hydrogenation of trifluoromethylcyclohexyl ketone on cinchona alkaloid modified pt-alumina catalyst

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Abstract

The enantioselective heterogeneous catalytic hydrogenation of trifluoromethylcyclohexyl ketone (2), on Pt-alumina (E4759) modified by different chiral compounds in toluene and ethanol solution with and without trifluoroacetic (TFA) has been investigated. The effects of the type of modifiers and their concentration (0-10 mmol/l), hydrogen pressure (1-100 bar), temperature (273-301 K) and conversion on the reaction rate and the enantioselectivity (ee) were studied. The achieved ee was 48% in the case of CD. Depending on solvents the inversion of enantioselectivity was observed. The available information suggests that the compounds responsible for chiral induction are different intermediates, the structure of which depends mostly on the acidic or non-acidic nature of the hydrogenation medium.

Original languageEnglish
Pages (from-to)65-70
Number of pages6
JournalCatalysis Letters
Volume97
Issue number1-2
DOIs
Publication statusPublished - Aug 2004

Fingerprint

Cinchona Alkaloids
alkaloids
Aluminum Oxide
Enantioselectivity
Ketones
ketones
Hydrogenation
hydrogenation
Alumina
aluminum oxides
catalysts
Catalysts
toluene
induction
reaction kinetics
ethyl alcohol
Toluene
inversions
Reaction rates
Hydrogen

Keywords

  • Cinchona alkaloids
  • Enantioselective
  • Fluoroketones
  • Hydrogenation
  • Intermediate complexes
  • Platinum-alumina

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

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abstract = "The enantioselective heterogeneous catalytic hydrogenation of trifluoromethylcyclohexyl ketone (2), on Pt-alumina (E4759) modified by different chiral compounds in toluene and ethanol solution with and without trifluoroacetic (TFA) has been investigated. The effects of the type of modifiers and their concentration (0-10 mmol/l), hydrogen pressure (1-100 bar), temperature (273-301 K) and conversion on the reaction rate and the enantioselectivity (ee) were studied. The achieved ee was 48{\%} in the case of CD. Depending on solvents the inversion of enantioselectivity was observed. The available information suggests that the compounds responsible for chiral induction are different intermediates, the structure of which depends mostly on the acidic or non-acidic nature of the hydrogenation medium.",
keywords = "Cinchona alkaloids, Enantioselective, Fluoroketones, Hydrogenation, Intermediate complexes, Platinum-alumina",
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T1 - Enantioselective hydrogenation of trifluoromethylcyclohexyl ketone on cinchona alkaloid modified pt-alumina catalyst

AU - Felföldi, K.

AU - Varga, Tibor

AU - Forgó, P.

AU - Bartók, M.

PY - 2004/8

Y1 - 2004/8

N2 - The enantioselective heterogeneous catalytic hydrogenation of trifluoromethylcyclohexyl ketone (2), on Pt-alumina (E4759) modified by different chiral compounds in toluene and ethanol solution with and without trifluoroacetic (TFA) has been investigated. The effects of the type of modifiers and their concentration (0-10 mmol/l), hydrogen pressure (1-100 bar), temperature (273-301 K) and conversion on the reaction rate and the enantioselectivity (ee) were studied. The achieved ee was 48% in the case of CD. Depending on solvents the inversion of enantioselectivity was observed. The available information suggests that the compounds responsible for chiral induction are different intermediates, the structure of which depends mostly on the acidic or non-acidic nature of the hydrogenation medium.

AB - The enantioselective heterogeneous catalytic hydrogenation of trifluoromethylcyclohexyl ketone (2), on Pt-alumina (E4759) modified by different chiral compounds in toluene and ethanol solution with and without trifluoroacetic (TFA) has been investigated. The effects of the type of modifiers and their concentration (0-10 mmol/l), hydrogen pressure (1-100 bar), temperature (273-301 K) and conversion on the reaction rate and the enantioselectivity (ee) were studied. The achieved ee was 48% in the case of CD. Depending on solvents the inversion of enantioselectivity was observed. The available information suggests that the compounds responsible for chiral induction are different intermediates, the structure of which depends mostly on the acidic or non-acidic nature of the hydrogenation medium.

KW - Cinchona alkaloids

KW - Enantioselective

KW - Fluoroketones

KW - Hydrogenation

KW - Intermediate complexes

KW - Platinum-alumina

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