Heterogeneous asymmetric reactions 34. New data in the enantioselective hydrogenation of ethyl pyruvate catalyzed by cinchona alkaloid-modified Pt/Al2O3 in toluene

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Abstract

The enantioselective hydrogenation of ethyl pyruvate (EtPy) on Pt-alumina (E 4759) catalyst modified by dihydrocinchonidine (DHCD) at a hydrogen pressure of 1 bar in toluene was studied. The effects of the modifier concentration (0.001-1 mmol1-1) and temperature (-10, 0, 24°C) on the reaction rate and the enantioselectivity have been studied. Under mild experimental conditions (hydrogen pressure: 1 bar, temperature: -10°C, DHCD concentration: 0.1 mmoll-1) an optical yield of 88% can be achieved. When EtPy hydrogenation was studied in AcOH under identical conditions, it was established that the DHCD/Ptsurf ratio necessary for achieving maximum enantioselectivity is highly solvent dependent: this ratio is 0.007 in AcOH and 0.12 in toluene. This large difference in DHCD/Ptsurf may be a reflection of a difference in reaction mechanism.

Original languageEnglish
Pages (from-to)235-240
Number of pages6
JournalCatalysis Letters
Volume87
Issue number3-4
DOIs
Publication statusPublished - Apr 2003

Fingerprint

Cinchona Alkaloids
pyruvates
alkaloids
Enantioselectivity
Toluene
Hydrogenation
hydrogenation
toluene
Hydrogen
Aluminum Oxide
hydrogen
Reaction rates
reaction kinetics
Alumina
aluminum oxides
catalysts
Temperature
Catalysts
temperature
ethyl pyruvate

Keywords

  • Cinchona alkaloids
  • Enantioselective
  • Ethyl pyruvate
  • Hydrogenation
  • Pt/AlO
  • Solvent effect

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

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title = "Heterogeneous asymmetric reactions 34. New data in the enantioselective hydrogenation of ethyl pyruvate catalyzed by cinchona alkaloid-modified Pt/Al2O3 in toluene",
abstract = "The enantioselective hydrogenation of ethyl pyruvate (EtPy) on Pt-alumina (E 4759) catalyst modified by dihydrocinchonidine (DHCD) at a hydrogen pressure of 1 bar in toluene was studied. The effects of the modifier concentration (0.001-1 mmol1-1) and temperature (-10, 0, 24°C) on the reaction rate and the enantioselectivity have been studied. Under mild experimental conditions (hydrogen pressure: 1 bar, temperature: -10°C, DHCD concentration: 0.1 mmoll-1) an optical yield of 88{\%} can be achieved. When EtPy hydrogenation was studied in AcOH under identical conditions, it was established that the DHCD/Ptsurf ratio necessary for achieving maximum enantioselectivity is highly solvent dependent: this ratio is 0.007 in AcOH and 0.12 in toluene. This large difference in DHCD/Ptsurf may be a reflection of a difference in reaction mechanism.",
keywords = "Cinchona alkaloids, Enantioselective, Ethyl pyruvate, Hydrogenation, Pt/AlO, Solvent effect",
author = "M. Bart{\'o}k and K. Bal{\'a}zsik and T. Bart{\'o}k and Z. Kele",
year = "2003",
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AU - Bartók, M.

AU - Balázsik, K.

AU - Bartók, T.

AU - Kele, Z.

PY - 2003/4

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N2 - The enantioselective hydrogenation of ethyl pyruvate (EtPy) on Pt-alumina (E 4759) catalyst modified by dihydrocinchonidine (DHCD) at a hydrogen pressure of 1 bar in toluene was studied. The effects of the modifier concentration (0.001-1 mmol1-1) and temperature (-10, 0, 24°C) on the reaction rate and the enantioselectivity have been studied. Under mild experimental conditions (hydrogen pressure: 1 bar, temperature: -10°C, DHCD concentration: 0.1 mmoll-1) an optical yield of 88% can be achieved. When EtPy hydrogenation was studied in AcOH under identical conditions, it was established that the DHCD/Ptsurf ratio necessary for achieving maximum enantioselectivity is highly solvent dependent: this ratio is 0.007 in AcOH and 0.12 in toluene. This large difference in DHCD/Ptsurf may be a reflection of a difference in reaction mechanism.

AB - The enantioselective hydrogenation of ethyl pyruvate (EtPy) on Pt-alumina (E 4759) catalyst modified by dihydrocinchonidine (DHCD) at a hydrogen pressure of 1 bar in toluene was studied. The effects of the modifier concentration (0.001-1 mmol1-1) and temperature (-10, 0, 24°C) on the reaction rate and the enantioselectivity have been studied. Under mild experimental conditions (hydrogen pressure: 1 bar, temperature: -10°C, DHCD concentration: 0.1 mmoll-1) an optical yield of 88% can be achieved. When EtPy hydrogenation was studied in AcOH under identical conditions, it was established that the DHCD/Ptsurf ratio necessary for achieving maximum enantioselectivity is highly solvent dependent: this ratio is 0.007 in AcOH and 0.12 in toluene. This large difference in DHCD/Ptsurf may be a reflection of a difference in reaction mechanism.

KW - Cinchona alkaloids

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KW - Hydrogenation

KW - Pt/AlO

KW - Solvent effect

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