Effect of the substituent position on the enantioselective hydrogenation of methoxy-substituted 2,3-diphenylpropenoic acids over palladium catalyst

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Abstract

The enantioselective hydrogenation of mono and dimethoxy-substituted 2,3-diphenylpropenoic acids has been studied over cinchonidine modified supported Pd catalyst. The hydrogenation of the six monosubstituted methoxy derivatives of (E)-2,3-diphenylpropenoic acid showed that the position of the substituent has a decisive influence on the initial reaction rate and the enantioselectivity. High enantioselectivities, 86-90%, were obtained in the hydrogenation of mono-substituted derivatives with a favourable substituent position. The results were rationalized in terms of either the electronic or the steric effects of the methoxy substituent determined by its position. These suggestions were also applicable in interpreting the results obtained in the hydrogenation of substituted (Z)-2,3-diphenylpropenoic acids and selected dimethoxy (E)-2,3-diphenylpropenoic acids. The combined steric and electronic effects of the substituents on the α- and β-phenyl rings ensured the highest enantioselectivities, up to 92% ee, in the hydrogenation of (E)-2-(2-methoxyphenyl)-3-(4-methoxyphenyl)propenoic acid.

Original languageEnglish
Pages (from-to)54-59
Number of pages6
JournalJournal of Molecular Catalysis A: Chemical
Volume290
Issue number1-2
DOIs
Publication statusPublished - Jul 1 2008

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Palladium
Hydrogenation
hydrogenation
palladium
Enantioselectivity
catalysts
acids
Catalysts
Acids
Derivatives
electronics
Catalyst supports
Reaction rates
suggestion
reaction kinetics
rings

Keywords

  • (E)-2,3-Diphenylpropenoic acid
  • Benzylamine
  • Cinchonidine
  • Enantioselective
  • Hydrogenation
  • Methoxy substituent
  • Palladium
  • Substituent position

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology
  • Materials Science (miscellaneous)

Cite this

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title = "Effect of the substituent position on the enantioselective hydrogenation of methoxy-substituted 2,3-diphenylpropenoic acids over palladium catalyst",
abstract = "The enantioselective hydrogenation of mono and dimethoxy-substituted 2,3-diphenylpropenoic acids has been studied over cinchonidine modified supported Pd catalyst. The hydrogenation of the six monosubstituted methoxy derivatives of (E)-2,3-diphenylpropenoic acid showed that the position of the substituent has a decisive influence on the initial reaction rate and the enantioselectivity. High enantioselectivities, 86-90{\%}, were obtained in the hydrogenation of mono-substituted derivatives with a favourable substituent position. The results were rationalized in terms of either the electronic or the steric effects of the methoxy substituent determined by its position. These suggestions were also applicable in interpreting the results obtained in the hydrogenation of substituted (Z)-2,3-diphenylpropenoic acids and selected dimethoxy (E)-2,3-diphenylpropenoic acids. The combined steric and electronic effects of the substituents on the α- and β-phenyl rings ensured the highest enantioselectivities, up to 92{\%} ee, in the hydrogenation of (E)-2-(2-methoxyphenyl)-3-(4-methoxyphenyl)propenoic acid.",
keywords = "(E)-2,3-Diphenylpropenoic acid, Benzylamine, Cinchonidine, Enantioselective, Hydrogenation, Methoxy substituent, Palladium, Substituent position",
author = "G. Sz{\"o}llősi and Be{\'a}ta Herm{\'a}n and K. Felf{\"o}ldi and F. F{\"u}l{\"o}p and M. Bart{\'o}k",
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TY - JOUR

T1 - Effect of the substituent position on the enantioselective hydrogenation of methoxy-substituted 2,3-diphenylpropenoic acids over palladium catalyst

AU - Szöllősi, G.

AU - Hermán, Beáta

AU - Felföldi, K.

AU - Fülöp, F.

AU - Bartók, M.

PY - 2008/7/1

Y1 - 2008/7/1

N2 - The enantioselective hydrogenation of mono and dimethoxy-substituted 2,3-diphenylpropenoic acids has been studied over cinchonidine modified supported Pd catalyst. The hydrogenation of the six monosubstituted methoxy derivatives of (E)-2,3-diphenylpropenoic acid showed that the position of the substituent has a decisive influence on the initial reaction rate and the enantioselectivity. High enantioselectivities, 86-90%, were obtained in the hydrogenation of mono-substituted derivatives with a favourable substituent position. The results were rationalized in terms of either the electronic or the steric effects of the methoxy substituent determined by its position. These suggestions were also applicable in interpreting the results obtained in the hydrogenation of substituted (Z)-2,3-diphenylpropenoic acids and selected dimethoxy (E)-2,3-diphenylpropenoic acids. The combined steric and electronic effects of the substituents on the α- and β-phenyl rings ensured the highest enantioselectivities, up to 92% ee, in the hydrogenation of (E)-2-(2-methoxyphenyl)-3-(4-methoxyphenyl)propenoic acid.

AB - The enantioselective hydrogenation of mono and dimethoxy-substituted 2,3-diphenylpropenoic acids has been studied over cinchonidine modified supported Pd catalyst. The hydrogenation of the six monosubstituted methoxy derivatives of (E)-2,3-diphenylpropenoic acid showed that the position of the substituent has a decisive influence on the initial reaction rate and the enantioselectivity. High enantioselectivities, 86-90%, were obtained in the hydrogenation of mono-substituted derivatives with a favourable substituent position. The results were rationalized in terms of either the electronic or the steric effects of the methoxy substituent determined by its position. These suggestions were also applicable in interpreting the results obtained in the hydrogenation of substituted (Z)-2,3-diphenylpropenoic acids and selected dimethoxy (E)-2,3-diphenylpropenoic acids. The combined steric and electronic effects of the substituents on the α- and β-phenyl rings ensured the highest enantioselectivities, up to 92% ee, in the hydrogenation of (E)-2-(2-methoxyphenyl)-3-(4-methoxyphenyl)propenoic acid.

KW - (E)-2,3-Diphenylpropenoic acid

KW - Benzylamine

KW - Cinchonidine

KW - Enantioselective

KW - Hydrogenation

KW - Methoxy substituent

KW - Palladium

KW - Substituent position

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U2 - 10.1016/j.molcata.2008.05.004

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