Stereodifferentiation in heterogeneous catalytic hydrogenation. Kinetic resolution and asymmetric hydrogenation in the presence of (S)-proline

Catalyst-dependent processes

Nóra Gyorffy, A. Tungler, Mátyás Fodor

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The kinetic resolution of 3,5,5-trimethyl cyclohexanone (TMCH) and asymmetric hydrogenation of isophorone (3,5,5-trimethyl cyclohex-2-enone, IP) were investigated on different Pd catalysts in the presence of (S)-proline (Pr). It could be proven that in isophorone hydrogenation the optically active TMCH was formed not only by kinetic resolution but also through asymmetric C{double bond, long}C hydrogenation. The activity and stereoselectivity of different Pd catalysts depended on the support material, preparation method, and reaction conditions as well, confirming our assumption that enantiodifferentiation takes also place on the catalyst surface and not only in the homogeneous liquid phase condensation reaction.

Original languageEnglish
Pages (from-to)2-8
Number of pages7
JournalJournal of Catalysis
Volume270
Issue number1
DOIs
Publication statusPublished - Mar 22 2010

Fingerprint

Proline
Hydrogenation
hydrogenation
catalysts
Catalysts
Kinetics
kinetics
Stereoselectivity
Condensation reactions
Catalyst supports
liquid phases
Thermodynamic properties
condensation
preparation
Liquids
isophorone
cyclohexanone

Keywords

  • (S)-Proline
  • 3,5,5-Trimethyl cyclohexanone
  • Asymmetric C{double bond, long}C hydrogenation
  • Isophorone
  • Kinetic resolution
  • Palladium catalysts

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

Cite this

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abstract = "The kinetic resolution of 3,5,5-trimethyl cyclohexanone (TMCH) and asymmetric hydrogenation of isophorone (3,5,5-trimethyl cyclohex-2-enone, IP) were investigated on different Pd catalysts in the presence of (S)-proline (Pr). It could be proven that in isophorone hydrogenation the optically active TMCH was formed not only by kinetic resolution but also through asymmetric C{double bond, long}C hydrogenation. The activity and stereoselectivity of different Pd catalysts depended on the support material, preparation method, and reaction conditions as well, confirming our assumption that enantiodifferentiation takes also place on the catalyst surface and not only in the homogeneous liquid phase condensation reaction.",
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T1 - Stereodifferentiation in heterogeneous catalytic hydrogenation. Kinetic resolution and asymmetric hydrogenation in the presence of (S)-proline

T2 - Catalyst-dependent processes

AU - Gyorffy, Nóra

AU - Tungler, A.

AU - Fodor, Mátyás

PY - 2010/3/22

Y1 - 2010/3/22

N2 - The kinetic resolution of 3,5,5-trimethyl cyclohexanone (TMCH) and asymmetric hydrogenation of isophorone (3,5,5-trimethyl cyclohex-2-enone, IP) were investigated on different Pd catalysts in the presence of (S)-proline (Pr). It could be proven that in isophorone hydrogenation the optically active TMCH was formed not only by kinetic resolution but also through asymmetric C{double bond, long}C hydrogenation. The activity and stereoselectivity of different Pd catalysts depended on the support material, preparation method, and reaction conditions as well, confirming our assumption that enantiodifferentiation takes also place on the catalyst surface and not only in the homogeneous liquid phase condensation reaction.

AB - The kinetic resolution of 3,5,5-trimethyl cyclohexanone (TMCH) and asymmetric hydrogenation of isophorone (3,5,5-trimethyl cyclohex-2-enone, IP) were investigated on different Pd catalysts in the presence of (S)-proline (Pr). It could be proven that in isophorone hydrogenation the optically active TMCH was formed not only by kinetic resolution but also through asymmetric C{double bond, long}C hydrogenation. The activity and stereoselectivity of different Pd catalysts depended on the support material, preparation method, and reaction conditions as well, confirming our assumption that enantiodifferentiation takes also place on the catalyst surface and not only in the homogeneous liquid phase condensation reaction.

KW - (S)-Proline

KW - 3,5,5-Trimethyl cyclohexanone

KW - Asymmetric C{double bond, long}C hydrogenation

KW - Isophorone

KW - Kinetic resolution

KW - Palladium catalysts

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