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

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Abstract

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.

Original languageEnglish
Pages (from-to)421-424
Number of pages4
JournalCatalysis Communications
Volume9
Issue number3
DOIs
Publication statusPublished - Mar 1 2008

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Cinchona Alkaloids
Palladium
Carboxylic Acids
Carboxylic acids
Hydrogenation
Catalysts
Acids
Enantioselectivity
Crotonates

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology

Cite this

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title = "Enantioselective hydrogenation of fluorinated unsaturated carboxylic acids over cinchona alkaloid modified palladium catalysts",
abstract = "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.",
keywords = "Carboxylic acids, Cinchonidine, Enantioselective, Fluorinated, Heterogeneous catalyst, Hydrogenation, Palladium",
author = "G. Sz{\"o}llősi and Tibor Varga and K. Felf{\"o}ldi and S. Cser{\'e}nyi and M. Bart{\'o}k",
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T1 - Enantioselective hydrogenation of fluorinated unsaturated carboxylic acids over cinchona alkaloid modified palladium catalysts

AU - Szöllősi, G.

AU - Varga, Tibor

AU - Felföldi, K.

AU - Cserényi, S.

AU - Bartók, M.

PY - 2008/3/1

Y1 - 2008/3/1

N2 - 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.

AB - 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.

KW - Carboxylic acids

KW - Cinchonidine

KW - Enantioselective

KW - Fluorinated

KW - Heterogeneous catalyst

KW - Hydrogenation

KW - Palladium

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