Inversion of enantioselectivity in the hydrogenation of ketopantolactone on platinum modified by ether derivatives of cinchonidine

被引：59

作者：

Diezi, S

Szabo, A

Mallat, T

Baiker, A

机构：

[1] ETH Honggerberg, Inst Chem & Bioengn, Swiss Fed Inst Technol, CH-8093 Zurich, Switzerland

[2] Ubichem Res Ltd, H-1025 Budapest, Hungary

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 17期

关键词：

D O I：

10.1016/S0957-4166(03)00528-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric hydrogenation of ketopantolactone was studied on a 5 wt% Pt/Al2O3 catalyst in the presence of cinchonidine and its O-methyl. -ethyl. -phenyl and -trimethylsilyl derivatives. Inversion of enantioselectivity with the latter two bulky substituents proved that in the enantiodifferentiating step cinchonidine adsorbs via the quinoline ring lying approximately parallel to the Pt surface. The striking nonlinear effect observed with cinchonidine-O-phenyl-cinchonidine mixtures is attributed to differences in the adsorption strength and geometry of the modifiers. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：2573 / 2577

页数：5

相关论文

共 41 条

[1] SYNTHESES AND CRYSTAL-STRUCTURES OF THE CINCHONA ALKALOID DERIVATIVES USED AS LIGANDS IN THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION OF OLEFINS [J].

AMBERG, W ;

BENNANI, YL ;

CHADHA, RK ;

CRISPINO, GA ;

DAVIS, WD ;

HARTUNG, J ;

JEONG, KS ;

OGINO, Y ;

SHIBATA, T ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (04) :844-849

[2] Adsorption of cinchonidine on platinum:: an electrochemical study [J].

Bakos, I ;

Szabó, S ;

Bartók, M ;

Kálmán, E .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2002, 532 (1-2) :113-119

[3] ENANTIOSELECTIVE HYDROGENATION .4. HYDROGEN ISOTOPE-EXCHANGE IN 10,11-DIHYDROCINCHONIDINE AND IN QUINOLINE CATALYZED BY PLATINUM-GROUP METALS [J].

BOND, G ;

WELLS, PB .

JOURNAL OF CATALYSIS, 1994, 150 (02) :329-334

[4]

Brunner H, 2001, EUR J INORG CHEM, P917

[5] Asymmetric catalysis. Part 128: Diastereomeric rhodium(I) complexes in the enantioselective hydrogenation of ketopantolactone [J].

Brunner, H ;

Tracht, T .

TETRAHEDRON-ASYMMETRY, 1998, 9 (21) :3773-3780

[6] Adsorption of ethyl pyruvate on Pt(111) studied by XPS and UPS [J].

Bürgi, T ;

Atamny, F ;

Schlögl, R ;

Baiker, A .

JOURNAL OF PHYSICAL CHEMISTRY B, 2000, 104 (25) :5953-5960

[7] XPS AND LEED STUDIES OF 10,11-DIHYDROCINCHONIDINE ADSORPTION AT PT(111) - IMPLICATIONS FOR THE ROLE OF CINCHONA ALKALOIDS IN ENANTIOSELECTIVE HYDROGENATION [J].

CARLEY, AF ;

RAJUMON, MK ;

ROBERTS, MW ;

WELLS, PB .

JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1995, 91 (14) :2167-2172

[8] In-situ Raman investigation of cinchonidine adsorption on polycrystalline platinum in ethanol [J].

Chu, W ;

LeBlanc, RJ ;

Williams, CT .

CATALYSIS COMMUNICATIONS, 2002, 3 (12) :547-552

[9] Orientation of 10,11-dihydrocinchonidine on Pt(111) [J].

Evans, T ;

Woodhead, AP ;

Gutiérrez-Sosa, A ;

Thornton, G ;

Hall, TJ ;

Davis, AA ;

Young, NA ;

Wells, PB ;

Oldman, RJ ;

Plashkevych, O ;

Vahtras, O ;

Ågren, H ;

Carravetta, V .

SURFACE SCIENCE, 1999, 436 (1-3) :L691-L696

[10] Chiral modification of platinum catalysts by cinchonidine adsorption studied by in situ ATR-IR spectroscopy [J].

Ferri, D ;

Bürgi, T ;

Baiker, A .

CHEMICAL COMMUNICATIONS, 2001, (13) :1172-1173

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