Modifier-substrate interactions of various types in the Orito reaction: Reversal of the enantioselection in the hydrogenation of ketopantolactone on Pt modified by β-isocinchonine and O-phenylcinchonidine

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Abstract

The enantioselective hydrogenation of ketopantolactone (KPL) on Pt-alumina catalyst modified by β-isocinchonine (β-ICN) and O-phenylcinchonidine (PhOCD) in toluene, acetic acid and their mixtures under otherwise identical experimental conditions was studied. Reversal of the enantioselection was obtained dependent on the concentration of acetic acid (eemax = 17% (S) on Pt-PhOCD and 50% (R) on Pt-β-ICN, respectively). The possible role in enantioselection of adducts forming in the reaction mixture and the stability of PhOCD under the conditions of the hydrogenation was investigated by ESI-MS. The results of the nonlinear phenomenon measurements on β-ICN + PhOCD mixtures suggest that the intermediate surface complexes β-ICN-KPL and PhOCD-KPL responsible for the opposite enantioselection include different types of interactions and the enantioselection is directed by the competition between these interactions.

Original languageEnglish
Pages (from-to)81-85
Number of pages5
JournalCatalysis Communications
Volume32
DOIs
Publication statusPublished - Feb 5 2013

Fingerprint

Hydrogenation
Acetic acid
Acetic Acid
Substrates
Aluminum Oxide
Toluene
Alumina
Catalysts
keto-pantoyllactone

Keywords

  • Cinchona alkaloid
  • Enantioselective hydrogenation
  • Intermediate complexes
  • Ketopantolactone
  • Keywords
  • Platinum
  • Reversal of enantioselectivity

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology
  • Chemistry(all)

Cite this

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title = "Modifier-substrate interactions of various types in the Orito reaction: Reversal of the enantioselection in the hydrogenation of ketopantolactone on Pt modified by β-isocinchonine and O-phenylcinchonidine",
abstract = "The enantioselective hydrogenation of ketopantolactone (KPL) on Pt-alumina catalyst modified by β-isocinchonine (β-ICN) and O-phenylcinchonidine (PhOCD) in toluene, acetic acid and their mixtures under otherwise identical experimental conditions was studied. Reversal of the enantioselection was obtained dependent on the concentration of acetic acid (eemax = 17{\%} (S) on Pt-PhOCD and 50{\%} (R) on Pt-β-ICN, respectively). The possible role in enantioselection of adducts forming in the reaction mixture and the stability of PhOCD under the conditions of the hydrogenation was investigated by ESI-MS. The results of the nonlinear phenomenon measurements on β-ICN + PhOCD mixtures suggest that the intermediate surface complexes β-ICN-KPL and PhOCD-KPL responsible for the opposite enantioselection include different types of interactions and the enantioselection is directed by the competition between these interactions.",
keywords = "Cinchona alkaloid, Enantioselective hydrogenation, Intermediate complexes, Ketopantolactone, Keywords, Platinum, Reversal of enantioselectivity",
author = "G. Sz{\"o}llősi and K. Bal{\'a}zsik and I. Bucsi and T. Bart{\'o}k and M. Bart{\'o}k",
year = "2013",
month = "2",
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language = "English",
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T1 - Modifier-substrate interactions of various types in the Orito reaction

T2 - Reversal of the enantioselection in the hydrogenation of ketopantolactone on Pt modified by β-isocinchonine and O-phenylcinchonidine

AU - Szöllősi, G.

AU - Balázsik, K.

AU - Bucsi, I.

AU - Bartók, T.

AU - Bartók, M.

PY - 2013/2/5

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N2 - The enantioselective hydrogenation of ketopantolactone (KPL) on Pt-alumina catalyst modified by β-isocinchonine (β-ICN) and O-phenylcinchonidine (PhOCD) in toluene, acetic acid and their mixtures under otherwise identical experimental conditions was studied. Reversal of the enantioselection was obtained dependent on the concentration of acetic acid (eemax = 17% (S) on Pt-PhOCD and 50% (R) on Pt-β-ICN, respectively). The possible role in enantioselection of adducts forming in the reaction mixture and the stability of PhOCD under the conditions of the hydrogenation was investigated by ESI-MS. The results of the nonlinear phenomenon measurements on β-ICN + PhOCD mixtures suggest that the intermediate surface complexes β-ICN-KPL and PhOCD-KPL responsible for the opposite enantioselection include different types of interactions and the enantioselection is directed by the competition between these interactions.

AB - The enantioselective hydrogenation of ketopantolactone (KPL) on Pt-alumina catalyst modified by β-isocinchonine (β-ICN) and O-phenylcinchonidine (PhOCD) in toluene, acetic acid and their mixtures under otherwise identical experimental conditions was studied. Reversal of the enantioselection was obtained dependent on the concentration of acetic acid (eemax = 17% (S) on Pt-PhOCD and 50% (R) on Pt-β-ICN, respectively). The possible role in enantioselection of adducts forming in the reaction mixture and the stability of PhOCD under the conditions of the hydrogenation was investigated by ESI-MS. The results of the nonlinear phenomenon measurements on β-ICN + PhOCD mixtures suggest that the intermediate surface complexes β-ICN-KPL and PhOCD-KPL responsible for the opposite enantioselection include different types of interactions and the enantioselection is directed by the competition between these interactions.

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KW - Reversal of enantioselectivity

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