Diastereoselective and enantioselective heterogeneous catalytic hydrogenation of aminocinnamic acid derivatives

A. Tungler, Á Fürcht, Zs P. Karancsi, G. Tóth, T. Máthé, L. Hegedús, Á Sándi

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13 Citations (Scopus)

Abstract

Various kinds of aminocinnamic acid derivatives were hydrogenated with different stereoselectivities. In the presence of cinchonidine or (-)- dihydroapovincaminic acid ethyl ester modifiers, the enantioselective hydrogenations resulted in very low enantiomeric excesses (ee). Moderate diastereomeric excesses (de, 5-68%) were achieved in the diastereoselective hydrogenations. The highest de (68%) was obtained in the hydrogenation of N- acetyldehydrophenylalanyl-(S)-prolinanilide due to a 10-member intermediate stabilized by hydrogen bond.

Original languageEnglish
Pages (from-to)239-244
Number of pages6
JournalJournal of Molecular Catalysis A: Chemical
Volume139
Issue number2-3
DOIs
Publication statusPublished - Mar 5 1999

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Keywords

  • Aminocinnamic acid
  • Asymmetric
  • Diastereoselective
  • Heterogeneous catalytic hydrogenation

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology
  • Physical and Theoretical Chemistry

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