Heterogeneous asymmetric reactions, 33. Novel interpretation of the enantioselective hydrogenation of α-ketoesters on Pt/alumina-cinchona alkaloid catalyst system

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Abstract

The enantioselective hydrogenation of ethyl pyruvate (EtPy) was studied in toluene and in acetic acid, under identical reaction conditions (H2 pressure 1 bar, Pt-alumina catalyst E 4759, dihydrocinchonidine (DHCD) concentration 0.001-0.1 mmol/L). The DHCD concentration necessary for achieving maximal enantioselectivity (i.e. 80% ee in toluene and 90% ee in acetic acid) is higher by one order to magnitude in toluene than in acetic acid. This relatively high difference suggests a difference in reaction mechanism. This study calls attention to the formation of new chiral surface sites via chemisorption of DHCD on platinum atoms and the possible role of such sites in enantioselection.

Original languageEnglish
Pages (from-to)363-370
Number of pages8
JournalReaction Kinetics and Catalysis Letters
Volume77
Issue number2
DOIs
Publication statusPublished - 2002

Fingerprint

Cinchona Alkaloids
alkaloids
Aluminum Oxide
Toluene
acetic acid
Acetic acid
Acetic Acid
Hydrogenation
hydrogenation
toluene
Alumina
aluminum oxides
catalysts
Catalysts
pyruvates
Enantioselectivity
Chemisorption
Platinum
chemisorption
platinum

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

Cite this

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title = "Heterogeneous asymmetric reactions, 33. Novel interpretation of the enantioselective hydrogenation of α-ketoesters on Pt/alumina-cinchona alkaloid catalyst system",
abstract = "The enantioselective hydrogenation of ethyl pyruvate (EtPy) was studied in toluene and in acetic acid, under identical reaction conditions (H2 pressure 1 bar, Pt-alumina catalyst E 4759, dihydrocinchonidine (DHCD) concentration 0.001-0.1 mmol/L). The DHCD concentration necessary for achieving maximal enantioselectivity (i.e. 80{\%} ee in toluene and 90{\%} ee in acetic acid) is higher by one order to magnitude in toluene than in acetic acid. This relatively high difference suggests a difference in reaction mechanism. This study calls attention to the formation of new chiral surface sites via chemisorption of DHCD on platinum atoms and the possible role of such sites in enantioselection.",
keywords = "Chemisorption model, Cinchona alkaloids, Enantioselective, Ethyl pyruvate, Hydrogenation, Pt/AlO, Solvent effect",
author = "M. Bart{\'o}k and K. Bal{\'a}zsik and F. Notheisz",
year = "2002",
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language = "English",
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pages = "363--370",
journal = "Reaction Kinetics, Mechanisms and Catalysis",
issn = "1878-5190",
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T1 - Heterogeneous asymmetric reactions, 33. Novel interpretation of the enantioselective hydrogenation of α-ketoesters on Pt/alumina-cinchona alkaloid catalyst system

AU - Bartók, M.

AU - Balázsik, K.

AU - Notheisz, F.

PY - 2002

Y1 - 2002

N2 - The enantioselective hydrogenation of ethyl pyruvate (EtPy) was studied in toluene and in acetic acid, under identical reaction conditions (H2 pressure 1 bar, Pt-alumina catalyst E 4759, dihydrocinchonidine (DHCD) concentration 0.001-0.1 mmol/L). The DHCD concentration necessary for achieving maximal enantioselectivity (i.e. 80% ee in toluene and 90% ee in acetic acid) is higher by one order to magnitude in toluene than in acetic acid. This relatively high difference suggests a difference in reaction mechanism. This study calls attention to the formation of new chiral surface sites via chemisorption of DHCD on platinum atoms and the possible role of such sites in enantioselection.

AB - The enantioselective hydrogenation of ethyl pyruvate (EtPy) was studied in toluene and in acetic acid, under identical reaction conditions (H2 pressure 1 bar, Pt-alumina catalyst E 4759, dihydrocinchonidine (DHCD) concentration 0.001-0.1 mmol/L). The DHCD concentration necessary for achieving maximal enantioselectivity (i.e. 80% ee in toluene and 90% ee in acetic acid) is higher by one order to magnitude in toluene than in acetic acid. This relatively high difference suggests a difference in reaction mechanism. This study calls attention to the formation of new chiral surface sites via chemisorption of DHCD on platinum atoms and the possible role of such sites in enantioselection.

KW - Chemisorption model

KW - Cinchona alkaloids

KW - Enantioselective

KW - Ethyl pyruvate

KW - Hydrogenation

KW - Pt/AlO

KW - Solvent effect

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