New data on the orito reaction: Effect of substrate structure on nonlinear phenomenon

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15 Citations (Scopus)

Abstract

The nonlinear phenomenon (NLP) was studied for the first time in the enantioselective hydrogenation of ethyl pyruvate (EP) and ketopantolactone (KPL) under identical conditions, on Pt catalyst modified by quinine and cinchonine, and for comparison with cinchonidine-cinchonine pair. The data obtained using the three methods allowed recognition of a new observation, namely that the NLP depends not only on the chiral modifier but also on the substrate to be hydrogenated. This observation can presumably be interpreted on the basis of differences in the structure of the substrate-modifier complexes formed and in the adsorption-desorption processes of the complexes, thus the NLP is not solely dependent on the adsorption of cinchona alkaloids, as suggested by earlier experimental data.

Original languageEnglish
Pages (from-to)401-407
Number of pages7
JournalCatalysis Letters
Volume125
Issue number3-4
DOIs
Publication statusPublished - Oct 2008

Fingerprint

Cinchona Alkaloids
Adsorption
Quinine
Substrates
Hydrogenation
Desorption
Catalysts
cinchonine
ethyl pyruvate
cinchonidine
keto-pantoyllactone

Keywords

  • Asymmetric hydrogenation
  • Cinchona alkaloids
  • Ethyl pyruvate
  • Ketopantolactone
  • Nonlinear phenomenon
  • Platinum

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

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title = "New data on the orito reaction: Effect of substrate structure on nonlinear phenomenon",
abstract = "The nonlinear phenomenon (NLP) was studied for the first time in the enantioselective hydrogenation of ethyl pyruvate (EP) and ketopantolactone (KPL) under identical conditions, on Pt catalyst modified by quinine and cinchonine, and for comparison with cinchonidine-cinchonine pair. The data obtained using the three methods allowed recognition of a new observation, namely that the NLP depends not only on the chiral modifier but also on the substrate to be hydrogenated. This observation can presumably be interpreted on the basis of differences in the structure of the substrate-modifier complexes formed and in the adsorption-desorption processes of the complexes, thus the NLP is not solely dependent on the adsorption of cinchona alkaloids, as suggested by earlier experimental data.",
keywords = "Asymmetric hydrogenation, Cinchona alkaloids, Ethyl pyruvate, Ketopantolactone, Nonlinear phenomenon, Platinum",
author = "K. Bal{\'a}zsik and S. Cser{\'e}nyi and G. Sz{\"o}llősi and F. F{\"u}l{\"o}p and M. Bart{\'o}k",
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TY - JOUR

T1 - New data on the orito reaction

T2 - Effect of substrate structure on nonlinear phenomenon

AU - Balázsik, K.

AU - Cserényi, S.

AU - Szöllősi, G.

AU - Fülöp, F.

AU - Bartók, M.

PY - 2008/10

Y1 - 2008/10

N2 - The nonlinear phenomenon (NLP) was studied for the first time in the enantioselective hydrogenation of ethyl pyruvate (EP) and ketopantolactone (KPL) under identical conditions, on Pt catalyst modified by quinine and cinchonine, and for comparison with cinchonidine-cinchonine pair. The data obtained using the three methods allowed recognition of a new observation, namely that the NLP depends not only on the chiral modifier but also on the substrate to be hydrogenated. This observation can presumably be interpreted on the basis of differences in the structure of the substrate-modifier complexes formed and in the adsorption-desorption processes of the complexes, thus the NLP is not solely dependent on the adsorption of cinchona alkaloids, as suggested by earlier experimental data.

AB - The nonlinear phenomenon (NLP) was studied for the first time in the enantioselective hydrogenation of ethyl pyruvate (EP) and ketopantolactone (KPL) under identical conditions, on Pt catalyst modified by quinine and cinchonine, and for comparison with cinchonidine-cinchonine pair. The data obtained using the three methods allowed recognition of a new observation, namely that the NLP depends not only on the chiral modifier but also on the substrate to be hydrogenated. This observation can presumably be interpreted on the basis of differences in the structure of the substrate-modifier complexes formed and in the adsorption-desorption processes of the complexes, thus the NLP is not solely dependent on the adsorption of cinchona alkaloids, as suggested by earlier experimental data.

KW - Asymmetric hydrogenation

KW - Cinchona alkaloids

KW - Ethyl pyruvate

KW - Ketopantolactone

KW - Nonlinear phenomenon

KW - Platinum

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