Reactions of chlorine substituted (E)-2,3-diphenylpropenoic acids over cinchonidine-modified Pd: Enantioselective hydrogenation versus hydrodechlorination

György Szllsi, Beáta Hermán, Erika Szabados, Ferenc Fülöp, Mihály Bartók

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The effect of the chlorine position on the C-Cl bond hydrogenolysis and the enantioselective hydrogenation of Cl substituted (E)-2,3-diphenylpropenoic acid derivatives has been studied over cinchonidine-modified Pd/Al2O 3. In contrast to the fast hydrodechlorination of the β-phenyl-para-Cl substituted acids the Cl on the α-phenyl ring was barely hydrogenolized. These observations were interpreted by the different arrangements of the two phenyl rings on the surface, with the α- and β-phenyl rings adsorbed tilted and parallel, respectively. The results confirmed the beneficial effect of the α-phenyl-ortho-substituents on the chiral discrimination, thus the 2,3-diphenylpropionic acids substituted by Cl on the α-phenyl ring could be prepared in good yields and optical purities. The conclusions were used for the rational design of an acid, i.e. (E)-2-(2-methoxyphenyl)-3-(3,4-difluorophenyl)propenoic acid, which afforded the best optical purity (ee up to 95% at 295 K) described until now in this heterogeneous system.

Original languageEnglish
Pages (from-to)28-36
Number of pages9
JournalJournal of Molecular Catalysis A: Chemical
Volume333
Issue number1-2
DOIs
Publication statusPublished - Dec 1 2010

Keywords

  • (E)-2,3-Diphenylpropenoic acids
  • Chlorine-substituent
  • Cinchonidine
  • Enantioselective hydrogenation
  • Palladium

ASJC Scopus subject areas

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

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