Heterogeneous asymmetric reactions part 32. High enantioselectivities in the hydrogenation of activated ketones on cinchona alkaloid modified platinum-alumina catalysts

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Abstract

The modifier concentration dependence of rate and enantioselectivity (ee) was investigated of the diethyl-2-oxoglutarate (EOG) and pyruvaldehyde dimethyl acetal (PADA) hydrogenations catalyzed by cinchona alkaloid modified Pt-alumina catalysts. Using the E 4759 catalyst in acetic acid under mild experimental conditions (room temperature, hydrogen pressure 1 bar) an optical yield of 95-97% can be achieved. Recent studies on activated ketones of different structures (EtPy: ethyl pyruvate, EOG, EBF: ethyl benzoylformate, PADA) carried out under identical experimental conditions have called attention to the role of additional factors to be considered for the interpretation of the mechanism of Orito's reaction.

Original languageEnglish
Pages (from-to)163-170
Number of pages8
JournalJournal of Molecular Catalysis A: Chemical
Volume202
Issue number1-2
DOIs
Publication statusPublished - Aug 1 2003

Fingerprint

Cinchona Alkaloids
Pyruvaldehyde
acetals
alkaloids
Aluminum Oxide
Enantioselectivity
Platinum
Ketones
ketones
externally blown flaps
Hydrogenation
hydrogenation
platinum
Alumina
aluminum oxides
pyruvates
catalysts
Catalysts
acetic acid
Acetic acid

Keywords

  • Cinchona alkaloid
  • Diethyl 2-oxoglutarate
  • Enantioselective
  • Hydrogenation
  • Platinum-alumina
  • Pyruvaldehyde dimethyl acetal

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology

Cite this

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title = "Heterogeneous asymmetric reactions part 32. High enantioselectivities in the hydrogenation of activated ketones on cinchona alkaloid modified platinum-alumina catalysts",
abstract = "The modifier concentration dependence of rate and enantioselectivity (ee) was investigated of the diethyl-2-oxoglutarate (EOG) and pyruvaldehyde dimethyl acetal (PADA) hydrogenations catalyzed by cinchona alkaloid modified Pt-alumina catalysts. Using the E 4759 catalyst in acetic acid under mild experimental conditions (room temperature, hydrogen pressure 1 bar) an optical yield of 95-97{\%} can be achieved. Recent studies on activated ketones of different structures (EtPy: ethyl pyruvate, EOG, EBF: ethyl benzoylformate, PADA) carried out under identical experimental conditions have called attention to the role of additional factors to be considered for the interpretation of the mechanism of Orito's reaction.",
keywords = "Cinchona alkaloid, Diethyl 2-oxoglutarate, Enantioselective, Hydrogenation, Platinum-alumina, Pyruvaldehyde dimethyl acetal",
author = "K. Felf{\"o}ldi and K. Bal{\'a}zsik and M. Bart{\'o}k",
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T1 - Heterogeneous asymmetric reactions part 32. High enantioselectivities in the hydrogenation of activated ketones on cinchona alkaloid modified platinum-alumina catalysts

AU - Felföldi, K.

AU - Balázsik, K.

AU - Bartók, M.

PY - 2003/8/1

Y1 - 2003/8/1

N2 - The modifier concentration dependence of rate and enantioselectivity (ee) was investigated of the diethyl-2-oxoglutarate (EOG) and pyruvaldehyde dimethyl acetal (PADA) hydrogenations catalyzed by cinchona alkaloid modified Pt-alumina catalysts. Using the E 4759 catalyst in acetic acid under mild experimental conditions (room temperature, hydrogen pressure 1 bar) an optical yield of 95-97% can be achieved. Recent studies on activated ketones of different structures (EtPy: ethyl pyruvate, EOG, EBF: ethyl benzoylformate, PADA) carried out under identical experimental conditions have called attention to the role of additional factors to be considered for the interpretation of the mechanism of Orito's reaction.

AB - The modifier concentration dependence of rate and enantioselectivity (ee) was investigated of the diethyl-2-oxoglutarate (EOG) and pyruvaldehyde dimethyl acetal (PADA) hydrogenations catalyzed by cinchona alkaloid modified Pt-alumina catalysts. Using the E 4759 catalyst in acetic acid under mild experimental conditions (room temperature, hydrogen pressure 1 bar) an optical yield of 95-97% can be achieved. Recent studies on activated ketones of different structures (EtPy: ethyl pyruvate, EOG, EBF: ethyl benzoylformate, PADA) carried out under identical experimental conditions have called attention to the role of additional factors to be considered for the interpretation of the mechanism of Orito's reaction.

KW - Cinchona alkaloid

KW - Diethyl 2-oxoglutarate

KW - Enantioselective

KW - Hydrogenation

KW - Platinum-alumina

KW - Pyruvaldehyde dimethyl acetal

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