Enantioselective hydrogénation of N-acetyldehydroamino acids over supported palladium catalysts

G. Szöllősi, Emese Szabó, Mihály Bartó

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The enantioselective hydrogenation of two N-acetyldehydroamino acids over Cinchona alkaloid-modified, supported palladium catalysts has been studied. Moderate enantioselectivities, up to 36%, were obtained in the hydrogenation of 2-acetamidocinnamic acid over cinchonidine-modified Pd/TiO2 under low hydrogen pressure. Increase in the pressure or use of benzylamine as additive led to a gradual decrease in the enantiomeric excess and eventually inversion of the sense of the enantioselectivity. On the contrary, the optical purity of the product resulting from the hydrogenation of 2-acetamidoacrylic acid was significantly increased by addition of benzylamine to the reaction mixture. Enantiomeric excess values up to 58% and 60% were obtained over Pd/Al 2O3 modified by cinchonidine and cinchonine, respectively. These optical purities are the best obtained in the hydrogenation of dehydroamino acid derivatives over chirally modified heterogeneous metal catalysts.

Original languageEnglish
Pages (from-to)405-410
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume349
Issue number3
DOIs
Publication statusPublished - Feb 2007

Fingerprint

Palladium
Hydrogenation
Catalysts
Acids
Enantioselectivity
Cinchona Alkaloids
Hydrogen
Metals
Derivatives
benzylamine
cinchonidine

Keywords

  • Cinchona alkaloids
  • Enantioselectivity
  • Heterogeneous catalysis
  • Hydrogenation
  • N-acetyldehydroamino acid
  • Palladium catalyst

ASJC Scopus subject areas

  • Chemistry (miscellaneous)
  • Organic Chemistry
  • Catalysis

Cite this

Enantioselective hydrogénation of N-acetyldehydroamino acids over supported palladium catalysts. / Szöllősi, G.; Szabó, Emese; Bartó, Mihály.

In: Advanced Synthesis and Catalysis, Vol. 349, No. 3, 02.2007, p. 405-410.

Research output: Contribution to journalArticle

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AB - The enantioselective hydrogenation of two N-acetyldehydroamino acids over Cinchona alkaloid-modified, supported palladium catalysts has been studied. Moderate enantioselectivities, up to 36%, were obtained in the hydrogenation of 2-acetamidocinnamic acid over cinchonidine-modified Pd/TiO2 under low hydrogen pressure. Increase in the pressure or use of benzylamine as additive led to a gradual decrease in the enantiomeric excess and eventually inversion of the sense of the enantioselectivity. On the contrary, the optical purity of the product resulting from the hydrogenation of 2-acetamidoacrylic acid was significantly increased by addition of benzylamine to the reaction mixture. Enantiomeric excess values up to 58% and 60% were obtained over Pd/Al 2O3 modified by cinchonidine and cinchonine, respectively. These optical purities are the best obtained in the hydrogenation of dehydroamino acid derivatives over chirally modified heterogeneous metal catalysts.

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