Enantioselective hydrogenation of fluorinated unsaturated carboxylic acids over cinchona alkaloid modified palladium catalysts

  • Szollosi G
  • Varga T
  • Felföldi K
 et al. 
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The hydrogenation of trifluoromethyl substituted prochiral α,β-unsaturated carboxylic acids has been studied over cinchona alkaloid modified palladium heterogeneous catalysts. Low enantioselectivities were obtained in the hydrogenation of all three test compounds, 2-trifluoromethylacrylic acid, 4,4,4-trifluoro-3-methyl-2-butenoic acid and (E)-4,4,4-trifluoro-3-phenyl-2-butenoic acid, respectively. Significant increase in the enantioselectivity, up to 43%, was obtained in the hydrogenation of 4,4,4-trifluoro-3-methyl-2-butenoic acid by using benzylamine as additive. The presented results showed for the first time the possibility of enantioselective hydrogenation of α-unsubstituted β-disubstituted α,β-unsaturated carboxylic acids in the cinchonidine modified palladium catalytic system, that resulted in optically enriched saturated acids having the chiral center in β position. © 2007 Elsevier B.V. All rights reserved.

Author-supplied keywords

  • Carboxylic acids
  • Cinchonidine
  • Enantioselective
  • Fluorinated
  • Heterogeneous catalyst
  • Hydrogenation
  • Palladium

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  • György Szollosi

  • Tibor Varga

  • Károly Felföldi

  • Szabolcs Cserényi

  • Mihály Bartók

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