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

L. Hegedûs, Viktor Háda, A. Tungler, Tibor Máthé, L. Szepesy

Research output: Contribution to journalArticle

38 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 - Jun 26 2000

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Pyridines
Pyridine
Hydrogenation
Proline
Methanol
Esters
Palladium
Temperature
Carbon
Metals
Derivatives
Acids

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology

Cite this

Diastereoselective heterogeneous catalytic hydrogenation of N-heterocycles. Part I. Hydrogenation of pyridines. / Hegedûs, L.; Háda, Viktor; Tungler, A.; Máthé, Tibor; Szepesy, L.

In: Applied Catalysis A: General, Vol. 201, No. 1, 26.06.2000, p. 107-114.

Research output: Contribution to journalArticle

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AU - Máthé, Tibor

AU - Szepesy, L.

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AB - 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.

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