Racemization of Secondary-Amine-Containing Natural Products Using Heterogeneous Metal Catalysts

Barbara Kovács, Risto Savela, Karoliina Honkala, Dmitry Yu Murzin, Enikő Forró, Ferenc Fülöp, Reko Leino

Research output: Contribution to journalArticle


Heterogeneously catalyzed racemization reactions of the secondary amines (S)-1-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (salsolidine) and (S)-1-methyl-1,2,3,4-tetrahydro-ß-carboline were investigated using Pd, Pt, and Ir on carbon or Al2O3 supports. A comparison of kinetics and deactivation on selected platinum and iridium catalysts was performed. Furthermore, the relative stabilities of (S)-salsolidine and the corresponding imine on Pt(1 1 1) and Ir(1 1 1) surfaces were analyzed by density functional theory calculations. The racemization was faster on platinum and took place without detectable byproduct formation. Iridium, however, proved reusable and, in contrast to the platinum catalyst, deactivation at low catalyst concentration was not observed. Also, the physisorption of (S)-salsolidine and the imine was stronger on platinum than on iridium.

Original languageEnglish
Pages (from-to)2893-2899
Number of pages7
Issue number13
Publication statusPublished - Jul 9 2018


  • amines
  • iridium
  • platinum
  • racemization
  • supported catalysts

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Fingerprint Dive into the research topics of 'Racemization of Secondary-Amine-Containing Natural Products Using Heterogeneous Metal Catalysts'. Together they form a unique fingerprint.

  • Cite this