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

页码：2 / 8

页数：7

共 36 条

[21] A novel asymmetric heterogeneous catalytic reaction: hydrogenation of ethyl 2-acetoxyacrylate on cinchonidine modified Pd and Pt catalyst
K. Szőri
György Szöllősi
K. Felföldi
Mihály Bartók
Reaction Kinetics and Catalysis Letters, 2005, 84 (1): : 151 - 156
[22] A novel asymmetric heterogeneous catalytic reaction:: Hydrogenation of ethyl 2-acetoxyacrylate on cinchonidine modified Pd and Pt catalyst
Szori, K
Szöllosi, G
Felföldi, K
Bartók, M
REACTION KINETICS AND CATALYSIS LETTERS, 2005, 84 (01): : 151 - 156
[23] Enantioselective total synthesis of (S)-(+)-lennoxamine through asymmetric hydrogenation mediated by L-proline-tetrazole ruthenium catalyst
Mirabal-Gallardo, Yaneris
Pierola, Johanna
Shankaraiah, Nagula
Santos, Leonardo S.
TETRAHEDRON LETTERS, 2012, 53 (28) : 3672 - 3675
[24] (S)-α,α-diphenyl- and (S)-α,α-dinaphthyl-2-pyrrolidinemethanol as chiral modifiers in asymmetric heterogeneous catalytic hydrogenation of isophorone
Sípos, É
Tungler, A
Bitter, I
Kubinyi, M
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 186 (1-2) : 187 - 192
[25] HOMOGENEOUS AND HETEROGENEOUS CATALYTIC ASYMMETRIC REACTIONS .4. HYDROGENATION OF THE NI COMPLEXES OF CINNAMIC ACID SALTS OVER MRNI CATALYST
BARTOK, M
WITTMANN, G
BARTOK, GB
GONDOS, G
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 384 (03) : 385 - 395
[26] Heterogeneous asymmetric reactions.: Part 24.: Heterogeneous catalytic enantioselective hydrogenation of the C=N group over cinchona alkaloid modified palladium catalyst
Szöllösi, G
Kun, I
Bartók, M
CHIRALITY, 2001, 13 (10) : 619 - 624
[27] Convincing Catalytic Performance of Oxo-Tethered Ruthenium Complexes for Asymmetric Transfer Hydrogenation of Cyclic α-Halogenated Ketones through Dynamic Kinetic Resolution
Touge, Taichiro
Nara, Hideki
Kida, Michio
Matsumura, Kazuhiko
Kayaki, Yoshihito
ORGANIC LETTERS, 2021, 23 (08) : 3070 - 3075
[28] Heterogeneous asymmetric reactions Part 28.: Efficient and practical method for the preparation of (R)- and (S)-α-hydroxy esters by the enantioselective heterogeneous catalytic hydrogenation of α-ketoesters
Szöri, K
Sutyinszki, M
Felföldi, K
Bartók, M
APPLIED CATALYSIS A-GENERAL, 2002, 237 (1-2) : 275 - 280
[29] A novel asymmetric heterogeneous catalytic reaction: hydrogenation of ethyl 2-acetoxyacrylate on cinchonidine modified Pd and Pt catalyst (vol 84, pg 151, 2005)
不详
REACTION KINETICS MECHANISMS AND CATALYSIS, 2023, 136 (06) : 3299 - 3300
[30] SELECTIVE CATALYTIC-HYDROGENATION OF AROMATIC NITRO-GROUPS IN THE PRESENCE OF ACETYLENES - SYNTHESIS OF (3-AMINOPHENYL)ACETYLENE VIA HYDROGENATION OF DIMETHYLCARBINOL SUBSTITUTED (3-NITROPHENYL)ACETYLENE OVER HETEROGENEOUS METALLIC RUTHENIUM CATALYST
ONOPCHENKO, A
SABOURIN, ET
SELWITZ, CM
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (08): : 1233 - 1236

← 1 2 3 4 →