Reversal of the ee in enantioselective hydrogenation of activated ketones in continuous-flow fixed-bed reactor system

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Abstract

A study on the hydrogenation of ethyl pyruvate, methyl benzoylformate and 2,2,2-trifluoroacetophenone over Pt-cinchona alkaloid chiral catalysts and over the "unmodified" catalysts resulted after a cleaning step at 323 K of the chirally modified surfaces in continuous-flow fixed-bed reactor system is presented. According to these investigations the sense of the residual ee observed in the reactions carried out in the absence of modifiers over the catalysts rinsed after the chiral hydrogenations was influenced by the solvent and the structure of the activated ketone, pointing on the effect of these parameters on the structure of the adsorbed intermediate complexes and implicitly on the chiral induction.

Original languageEnglish
Pages (from-to)14-19
Number of pages6
JournalCatalysis Communications
Volume12
Issue number1
DOIs
Publication statusPublished - Oct 25 2010

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Ketones
Hydrogenation
Catalysts
Cinchona Alkaloids
Cleaning

Keywords

  • Activated ketones
  • Asymmetric hydrogenation
  • Cinchona alkaloids
  • Flow reactor
  • Platinum
  • Reversal of ee

ASJC Scopus subject areas

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

Cite this

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abstract = "A study on the hydrogenation of ethyl pyruvate, methyl benzoylformate and 2,2,2-trifluoroacetophenone over Pt-cinchona alkaloid chiral catalysts and over the {"}unmodified{"} catalysts resulted after a cleaning step at 323 K of the chirally modified surfaces in continuous-flow fixed-bed reactor system is presented. According to these investigations the sense of the residual ee observed in the reactions carried out in the absence of modifiers over the catalysts rinsed after the chiral hydrogenations was influenced by the solvent and the structure of the activated ketone, pointing on the effect of these parameters on the structure of the adsorbed intermediate complexes and implicitly on the chiral induction.",
keywords = "Activated ketones, Asymmetric hydrogenation, Cinchona alkaloids, Flow reactor, Platinum, Reversal of ee",
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T1 - Reversal of the ee in enantioselective hydrogenation of activated ketones in continuous-flow fixed-bed reactor system

AU - Cserényi, S.

AU - Szöllősi, G.

AU - Szöri, K.

AU - Fülöp, F.

AU - Bartók, M.

PY - 2010/10/25

Y1 - 2010/10/25

N2 - A study on the hydrogenation of ethyl pyruvate, methyl benzoylformate and 2,2,2-trifluoroacetophenone over Pt-cinchona alkaloid chiral catalysts and over the "unmodified" catalysts resulted after a cleaning step at 323 K of the chirally modified surfaces in continuous-flow fixed-bed reactor system is presented. According to these investigations the sense of the residual ee observed in the reactions carried out in the absence of modifiers over the catalysts rinsed after the chiral hydrogenations was influenced by the solvent and the structure of the activated ketone, pointing on the effect of these parameters on the structure of the adsorbed intermediate complexes and implicitly on the chiral induction.

AB - A study on the hydrogenation of ethyl pyruvate, methyl benzoylformate and 2,2,2-trifluoroacetophenone over Pt-cinchona alkaloid chiral catalysts and over the "unmodified" catalysts resulted after a cleaning step at 323 K of the chirally modified surfaces in continuous-flow fixed-bed reactor system is presented. According to these investigations the sense of the residual ee observed in the reactions carried out in the absence of modifiers over the catalysts rinsed after the chiral hydrogenations was influenced by the solvent and the structure of the activated ketone, pointing on the effect of these parameters on the structure of the adsorbed intermediate complexes and implicitly on the chiral induction.

KW - Activated ketones

KW - Asymmetric hydrogenation

KW - Cinchona alkaloids

KW - Flow reactor

KW - Platinum

KW - Reversal of ee

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