Enantioselective hydrogenation of propenoic acids bearing heteroaromatic substituents over cinchonidine modified Pd/alumina

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Abstract

The hydrogenation of two 2,3-diarylpropenoic acids bearing heteroaromatic substituents, i.e. (E)-2-phenyl-3-(2-furyl)propenoic acid and (E)-2-(3-pyridyl)-3-phenylpropenoic acid was studied over cinchonidine modified Pd catalyst for the first time. The 2-furyl substituted compound was selectively hydrogenated to 2-phenyl-3-(2-furyl)propionic acid in the presence of cinchonidine in up to 73% ee. The hydrogenation of the acid bearing 3-pyridyl substituent afforded lower ee as compared to (E)-2,3-diphenylpropenoic acid, reaching up to 61% in presence of benzylamine additive. The differences in the results were assumed to be due to the different adsorption strengths and modes of these acids and deviations in their interactions with the adsorbed modifier.

Original languageEnglish
Pages (from-to)1107-1110
Number of pages4
JournalCatalysis Communications
Volume10
Issue number7
DOIs
Publication statusPublished - Mar 10 2009

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Bearings (structural)
Aluminum Oxide
Hydrogenation
Alumina
Acids
Propionic acid
cinchonidine
Adsorption
Catalysts

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology
  • Chemistry(all)

Cite this

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title = "Enantioselective hydrogenation of propenoic acids bearing heteroaromatic substituents over cinchonidine modified Pd/alumina",
abstract = "The hydrogenation of two 2,3-diarylpropenoic acids bearing heteroaromatic substituents, i.e. (E)-2-phenyl-3-(2-furyl)propenoic acid and (E)-2-(3-pyridyl)-3-phenylpropenoic acid was studied over cinchonidine modified Pd catalyst for the first time. The 2-furyl substituted compound was selectively hydrogenated to 2-phenyl-3-(2-furyl)propionic acid in the presence of cinchonidine in up to 73{\%} ee. The hydrogenation of the acid bearing 3-pyridyl substituent afforded lower ee as compared to (E)-2,3-diphenylpropenoic acid, reaching up to 61{\%} in presence of benzylamine additive. The differences in the results were assumed to be due to the different adsorption strengths and modes of these acids and deviations in their interactions with the adsorbed modifier.",
keywords = "Carboxylic acids, Cinchonidine, Enantioselective, Heteroaromatic, Heterogeneous catalyst, Hydrogenation, Palladium",
author = "Be{\'a}ta Herm{\'a}n and G. Sz{\"o}llősi and K. Felf{\"o}ldi and F. F{\"u}l{\"o}p and M. Bart{\'o}k",
year = "2009",
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T1 - Enantioselective hydrogenation of propenoic acids bearing heteroaromatic substituents over cinchonidine modified Pd/alumina

AU - Hermán, Beáta

AU - Szöllősi, G.

AU - Felföldi, K.

AU - Fülöp, F.

AU - Bartók, M.

PY - 2009/3/10

Y1 - 2009/3/10

N2 - The hydrogenation of two 2,3-diarylpropenoic acids bearing heteroaromatic substituents, i.e. (E)-2-phenyl-3-(2-furyl)propenoic acid and (E)-2-(3-pyridyl)-3-phenylpropenoic acid was studied over cinchonidine modified Pd catalyst for the first time. The 2-furyl substituted compound was selectively hydrogenated to 2-phenyl-3-(2-furyl)propionic acid in the presence of cinchonidine in up to 73% ee. The hydrogenation of the acid bearing 3-pyridyl substituent afforded lower ee as compared to (E)-2,3-diphenylpropenoic acid, reaching up to 61% in presence of benzylamine additive. The differences in the results were assumed to be due to the different adsorption strengths and modes of these acids and deviations in their interactions with the adsorbed modifier.

AB - The hydrogenation of two 2,3-diarylpropenoic acids bearing heteroaromatic substituents, i.e. (E)-2-phenyl-3-(2-furyl)propenoic acid and (E)-2-(3-pyridyl)-3-phenylpropenoic acid was studied over cinchonidine modified Pd catalyst for the first time. The 2-furyl substituted compound was selectively hydrogenated to 2-phenyl-3-(2-furyl)propionic acid in the presence of cinchonidine in up to 73% ee. The hydrogenation of the acid bearing 3-pyridyl substituent afforded lower ee as compared to (E)-2,3-diphenylpropenoic acid, reaching up to 61% in presence of benzylamine additive. The differences in the results were assumed to be due to the different adsorption strengths and modes of these acids and deviations in their interactions with the adsorbed modifier.

KW - Carboxylic acids

KW - Cinchonidine

KW - Enantioselective

KW - Heteroaromatic

KW - Heterogeneous catalyst

KW - Hydrogenation

KW - Palladium

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JO - Catalysis Communications

JF - Catalysis Communications

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