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

被引：8

作者：

Herman, Beata ^{[1
,2
]}

Szollosi, Gyorgy ^{[1
]}

Felfoldi, Karoly ^{[3
]}

Fulop, Ferenc ^{[2
]}

Bartok, Milhalp ^{[1
,3
]}

机构：

[1] Univ Szeged, Hungarian Acad Sci, Stereochem Res Grp, H-6720 Szeged, Hungary

[2] Univ Szeged, Inst Pharmaceut Chem, H-6720 Szeged, Hungary

[3] Univ Szeged, Dept Organ Chem, H-6720 Szeged, Hungary

来源：

CATALYSIS COMMUNICATIONS | 2009年 / 10卷 / 07期

基金：

美国国家科学基金会;

关键词：

Carboxylic acids; Cinchonidine; Enantioselective; Heteroaromatic; Heterogeneous catalyst; Hydrogenation; Palladium; UNSATURATED CARBOXYLIC-ACIDS; MODIFIED PALLADIUM CATALYST; ASYMMETRIC HYDROGENATION; SELECTIVE HYDROGENATION; SOLVENTS;

D O I：

10.1016/j.catcom.2009.01.008

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

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. (C) 2009 Elsevier B. V. All rights reserved.

引用

页码：1107 / 1110

页数：4

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