Hydrogenation of cinchona alkaloids over supported Pt catalyst

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

The heterogeneous catalytic hydrogenation of two isomeric cinchona alkaloids, cinchonidine and cinchonine, was studied over Pt/Al2O3 in 1N H2SO4 solution under 100 bar H2 at 25°C. Cinchonidine was transformed into two diastereomeric hexahydroderivatives by hydrogenation of ring A (with N) of the quinoline moiety (yield over 95%, diastereomeric ratio 2/3), whereas hydrogenation of cinchonine resulted in the formation of three products, the major one being formed by the hydrogenation of ring B (without N) (yield 60%). The isolated hexahydroderivatives were investigated by 1H-13C-NMR, 1H-1H COSY, 1H-13C HetCOSY, and NOESY spectroscopy and were used as modifiers in the heterogeneous enantioselective hydrogenation of ethyl pyruvate and as catalysts in the Michael addition of ethyl 2-oxocyclopentanecarboxylate to methyl vinyl ketone.

Original languageEnglish
Pages (from-to)S82-S89
JournalChirality
Volume15
Issue numberSUPPL.
DOIs
Publication statusPublished - Aug 12 2003

Keywords

  • Ethyl pyruvate
  • Hexahydrocinchonidine
  • Hexahydrocinchonine
  • Hydrogenation
  • Michael addition
  • Pt-alumina

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Hydrogenation of cinchona alkaloids over supported Pt catalyst'. Together they form a unique fingerprint.

  • Cite this