Hydrogenation of a- and b-isocinchonines on Pt-alumina catalyst in acetic acid

Mária Sutyinszki, I. Bucsi

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The transformations of a-ICN and b-ICN were studied in the presence of hydrogen in AcOH over Pt-alumina catalyst under the conditions of the enantioselective hydrogenation of EtPy (hydrogen pressure 1-30 bar, temperature 298-323 K). It was established that the quinoline skeleton of the alkaloids is hydrogenated even under mild experimental conditions, whereas hydrogenolysis of the oxazacycloalkane structure only takes place at hydrogen pressures exceeding 1 bar. ESI-MS-MS, HPLC-ESI-ion-trap MS and NMR made possible the identification of several hydrogenated cinchona alkaloid derivatives with so far unknown structures. According to these experimental results, the conformation of isocinchona alkaloids remains unchanged under the conditions of the enantioselective hydrogenation of activated ketones, making them suitable for utilization as chiral modifiers of well-defined conformation.

Original languageEnglish
Pages (from-to)157-165
Number of pages9
JournalReaction Kinetics and Catalysis Letters
Volume84
Issue number1
DOIs
Publication statusPublished - Jan 2005

Fingerprint

alkaloids
Aluminum Oxide
acetic acid
Acetic acid
Acetic Acid
Hydrogenation
hydrogenation
Hydrogen
Alkaloids
Alumina
aluminum oxides
catalysts
Catalysts
Conformations
hydrogen
Cinchona Alkaloids
hydrogenolysis
Hydrogenolysis
quinoline
Ketones

Keywords

  • Electrospray ionization
  • HPLC
  • Hydrogenation
  • Ion-trap mass spectrometry
  • Isocinchona alkaloids
  • Platinum-alumina

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

Hydrogenation of a- and b-isocinchonines on Pt-alumina catalyst in acetic acid. / Sutyinszki, Mária; Bucsi, I.

In: Reaction Kinetics and Catalysis Letters, Vol. 84, No. 1, 01.2005, p. 157-165.

Research output: Contribution to journalArticle

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