Asymmetric hydrogenation of prochiral and kinetic resolution of chiral cyclohexanone derivatives with Pd catalysts

Erika Szabados, Nóra Gyorffy, A. Tungler, József Balla, László Könczöl

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

This paper focuses on the investigation of the role of catalytic and molecular factors determining the optical yield in the enantioselective hydrogenation of C=C double bonds in prochiral unsaturated ketones and in the kinetic resolution of racemates of chiral cyclic ketones with proline mediated reductive alkylation. The hydrogenation of two unsaturated methyl cyclohexenones, and the kinetic resolution of two saturated methyl cyclohexanones with proline were studied with different Pd catalysts. The aim was to find out the effects of catalyst modifiers and chiral auxiliary, beside that of the structure and the degree of substitution of the substrates on the stereochemical outcome and yield of these reactions.

Original languageEnglish
Pages (from-to)107-114
Number of pages8
JournalReaction Kinetics, Mechanisms and Catalysis
Volume111
Issue number1
DOIs
Publication statusPublished - Feb 2014

Fingerprint

Ketones
Proline
ketones
Hydrogenation
hydrogenation
Cyclohexanones
Derivatives
catalysts
Catalysts
Kinetics
alkylation
Alkylation
kinetics
Substitution reactions
substitutes
Substrates
cyclohexanone

Keywords

  • 2-Methyl cyclohexanone
  • 3-Methyl cyclohexanone
  • Asymmetric C=C hydrogenation
  • Kinetic resolution
  • Pd catalyst
  • Proline chiral auxiliary

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

Cite this

Asymmetric hydrogenation of prochiral and kinetic resolution of chiral cyclohexanone derivatives with Pd catalysts. / Szabados, Erika; Gyorffy, Nóra; Tungler, A.; Balla, József; Könczöl, László.

In: Reaction Kinetics, Mechanisms and Catalysis, Vol. 111, No. 1, 02.2014, p. 107-114.

Research output: Contribution to journalArticle

Szabados, Erika ; Gyorffy, Nóra ; Tungler, A. ; Balla, József ; Könczöl, László. / Asymmetric hydrogenation of prochiral and kinetic resolution of chiral cyclohexanone derivatives with Pd catalysts. In: Reaction Kinetics, Mechanisms and Catalysis. 2014 ; Vol. 111, No. 1. pp. 107-114.
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