Heterogeneous asymmetric reactions. 23. Enantioselective hydrogenation of ethyl pyruvate over cinchonine- and α-isocinchonine-modified platinum catalysts

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Abstract

The enantioselective hydrogenation of ethyl pyruvate to (S)-ethyl lactate over cinchonine- and α-isocinchonine-modified Pt/Al2O3 catalysts was studied as a function of modifier concentration and reaction temperature. The maximum enantioselectivities obtained under the applied mild conditions were 89% ee using cinchonine (0.014 mmol dm-3, 1 bar H2, 23 °C, 6% AcOH in toluene), and 76% ee in the case of α-isocinchonine (0.14 mmol dm-3, 1 bar H2 - 10°C, 69t AcOH in toluene). Since α-isocinchonine of rigid structure exists only in "anti-open" conformation these data provide additional experimental evidence to support the former suggestion concerning the dominating role of "anti-open" conformation in these cinchona-modified enantioselective hydrogenations.

Original languageEnglish
Pages (from-to)127-131
Number of pages5
JournalCatalysis Letters
Volume73
Issue number2-4
DOIs
Publication statusPublished - May 2001

Fingerprint

pyruvates
Toluene
Platinum
Hydrogenation
hydrogenation
Conformations
toluene
Cinchona
platinum
Rigid structures
catalysts
lactates
Catalysts
Enantioselectivity
rigid structures
suggestion
Temperature
temperature
cinchonine
ethyl pyruvate

Keywords

  • α-isocinchonine
  • Enantioselective
  • Ethyl pyruvate
  • Hydrogenation
  • Pt/AlO

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

Cite this

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title = "Heterogeneous asymmetric reactions. 23. Enantioselective hydrogenation of ethyl pyruvate over cinchonine- and α-isocinchonine-modified platinum catalysts",
abstract = "The enantioselective hydrogenation of ethyl pyruvate to (S)-ethyl lactate over cinchonine- and α-isocinchonine-modified Pt/Al2O3 catalysts was studied as a function of modifier concentration and reaction temperature. The maximum enantioselectivities obtained under the applied mild conditions were 89{\%} ee using cinchonine (0.014 mmol dm-3, 1 bar H2, 23 °C, 6{\%} AcOH in toluene), and 76{\%} ee in the case of α-isocinchonine (0.14 mmol dm-3, 1 bar H2 - 10°C, 69t AcOH in toluene). Since α-isocinchonine of rigid structure exists only in {"}anti-open{"} conformation these data provide additional experimental evidence to support the former suggestion concerning the dominating role of {"}anti-open{"} conformation in these cinchona-modified enantioselective hydrogenations.",
keywords = "α-isocinchonine, Enantioselective, Ethyl pyruvate, Hydrogenation, Pt/AlO",
author = "M. Bart{\'o}k and B{\'e}la T{\"o}r{\"o}k and K. Bal{\'a}zsik and T. Bart{\'o}k",
year = "2001",
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pages = "127--131",
journal = "Catalysis Letters",
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T1 - Heterogeneous asymmetric reactions. 23. Enantioselective hydrogenation of ethyl pyruvate over cinchonine- and α-isocinchonine-modified platinum catalysts

AU - Bartók, M.

AU - Török, Béla

AU - Balázsik, K.

AU - Bartók, T.

PY - 2001/5

Y1 - 2001/5

N2 - The enantioselective hydrogenation of ethyl pyruvate to (S)-ethyl lactate over cinchonine- and α-isocinchonine-modified Pt/Al2O3 catalysts was studied as a function of modifier concentration and reaction temperature. The maximum enantioselectivities obtained under the applied mild conditions were 89% ee using cinchonine (0.014 mmol dm-3, 1 bar H2, 23 °C, 6% AcOH in toluene), and 76% ee in the case of α-isocinchonine (0.14 mmol dm-3, 1 bar H2 - 10°C, 69t AcOH in toluene). Since α-isocinchonine of rigid structure exists only in "anti-open" conformation these data provide additional experimental evidence to support the former suggestion concerning the dominating role of "anti-open" conformation in these cinchona-modified enantioselective hydrogenations.

AB - The enantioselective hydrogenation of ethyl pyruvate to (S)-ethyl lactate over cinchonine- and α-isocinchonine-modified Pt/Al2O3 catalysts was studied as a function of modifier concentration and reaction temperature. The maximum enantioselectivities obtained under the applied mild conditions were 89% ee using cinchonine (0.014 mmol dm-3, 1 bar H2, 23 °C, 6% AcOH in toluene), and 76% ee in the case of α-isocinchonine (0.14 mmol dm-3, 1 bar H2 - 10°C, 69t AcOH in toluene). Since α-isocinchonine of rigid structure exists only in "anti-open" conformation these data provide additional experimental evidence to support the former suggestion concerning the dominating role of "anti-open" conformation in these cinchona-modified enantioselective hydrogenations.

KW - α-isocinchonine

KW - Enantioselective

KW - Ethyl pyruvate

KW - Hydrogenation

KW - Pt/AlO

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JO - Catalysis Letters

JF - Catalysis Letters

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