Diastereoselective heterogeneous catalytic hydrogenation of N-heterocycles. Part I. Hydrogenation of pyridines

László Hegedus, Viktor Háda, Antal Tungler, Tibor Máthé, László Szepesy

Research output: Article

39 Citations (Scopus)

Abstract

High diastereoselectivities were obtained in the heterogeneous catalytic hydrogenation of chiral picolinic and nicotinic acid derivatives with complete conversion, in non-acidic medium. The effects of catalytic metals, solvents, temperature and pressure on the conversion and the diastereomeric excess (d.e.) were investigated. The hydrogenation of N-picolinoyl-(S)-proline methyl ester (1) resulted in 79% d.e. over 10% Pd/C, in methanol, at moderate pressure and temperature (50 bar, 50 °C). Very high d.e. (94%) was achieved in the saturation of N-nicotinoyl-(S)-proline methyl ester (2) under similar conditions. The hydrogenation of quaternized 1 took place already at room temperature (RT) and 20 bar with almost complete diastereoselectivity (98%), over palladium on carbon, in methanol. These are successful examples of a diastereoselection in the hydrogenation of prochiral pyridines.

Original languageEnglish
Pages (from-to)107-114
Number of pages8
JournalApplied Catalysis A: General
Volume201
Issue number1
DOIs
Publication statusPublished - jún. 26 2000

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology

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