Stereodifferentiation in heterogeneous catalytic hydrogenation. Kinetic resolution and asymmetric hydrogenation in the presence of (S)-proline: Catalyst-dependent processes

被引：16
|
作者：
Gyorffy, Nora [1 ]
Tungler, Antal [1 ]
Fodor, Matyas [2 ]
机构：
[1] Hungarian Acad Sci, Inst Isotopes, H-1525 Budapest, Hungary
[2] Budapest Univ Technol & Econ, Dept Chem & Environm Proc Engn, Budapest, Hungary
来源：
JOURNAL OF CATALYSIS | 2010年 / 270卷 / 01期
关键词：
Kinetic resolution; 3,5,5-Trimethyl cyclohexanone; Asymmetric C=C hydrogenation; Isophorone; (S)-Proline; Palladium catalysts; EXOCYCLIC ALPHA; BETA-UNSATURATED KETONES; ENANTIOSELECTIVE HYDROGENATION; PROLINE; ISOPHORONE; PD; DECARBOXYLATION; MODIFIER;
D O I：
10.1016/j.jcat.2009.10.018
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 kinetic resolution of 3,5,5-trimethyl cyclohexanone (TMCH) and asymmetric hydrogenation of isophorone (3,5,5-trimethyl cyclohex-2-enone, IP) were investigated on different Pd catalysts in the presence of (S)-proline (Pr). It could be proven that in isophorone hydrogenation the optically active TMCH was formed not only by kinetic resolution but also through asymmetric C=C hydrogenation. The activity and stereoselectivity of different Pd catalysts depended on the support material, preparation method, and reaction conditions as well, confirming our assumption that enantiodifferentiation takes also place on the catalyst surface and not only in the homogeneous liquid phase condensation reaction. (C) 2010 Published by Elsevier Inc.
引用
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页码：2 / 8
页数：7
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