Enantioselective hydrogenation on chirally modified platinum:: New insight into the adsorption mode of the modifier

被引：29

作者：

Bürgi, T ^{[1
]}

Zhou, ZH ^{[1
]}

Künzle, N ^{[1
]}

Mallat, T ^{[1
]}

Baiker, A ^{[1
]}

机构：

[1] ETH Zentrum, Tech Chem Lab, CH-8092 Zurich, Switzerland

来源：

JOURNAL OF CATALYSIS | 1999年 / 183卷 / 02期

关键词：

cinchonidine; 9-deoxycinchonidine; 2-phenyl-9-deoxy-10,11-dihydrocinchonidine; ketopantolactone; ethyl pyruvate; platinum; enantioselective hydrogenation; adsorption state;

D O I：

10.1006/jcat.1999.2411

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：

A new modifier, 2-phenyl-9-deoxy-10,11-dihydrocinchonidine has been synthesized for the enantioselective hydrogenation of ketopantolactone and alpha-ketoesters over chirally modified Pt/alumina. The results indicate flat adsorption of cinchonidine with the quinoline ring oriented parallel to the surface and, furthermore, give some insight into the conformation of the modifier within the transition state complex. Comparison of the structures and catalytic behaviors of 9-deoxycinchonidine and the new modifier allows to exclude the previously proposed perpendicular or tilted adsorption of the quinoline ring via the N atom. (C) 1999 Academic Press.

引用

页码：405 / 408

页数：4

共 23 条

[1] [Anonymous], J CHEM SOC JPN
[2] ENANTIOSELECTIVE HETEROGENEOUS CATALYSIS .1. A WORKING MODEL FOR THE CATALYST-MODIFIER-SUBSTRATE INTERACTIONS IN CHIRAL PYRUVATE HYDROGENATIONS
AUGUSTINE, RL
TANIELYAN, SK
DOYLE, LK
[J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (08) : 1803 - 1827
[3] Progress in asymmetric heterogeneous catalysis: Design of novel chirally modified platinum metal catalysts
Baiker, A
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 115 (03) : 473 - 493
[4] BLASER HU, 1991, STUD SURF SCI CATAL, V67, P147, DOI 10.1016/S0167-2991(08)61934-5
[5] ENANTIOSELECTIVE HYDROGENATION .4. HYDROGEN ISOTOPE-EXCHANGE IN 10,11-DIHYDROCINCHONIDINE AND IN QUINOLINE CATALYZED BY PLATINUM-GROUP METALS
BOND, G
WELLS, PB
[J]. JOURNAL OF CATALYSIS, 1994, 150 (02) : 329 - 334
[6] Conformational behavior of cinchonidine in different solvents:: A combined NMR and ab initio investigation
Bürgi, T
Baiker, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) : 12920 - 12926
[7] Collins A. N., 1995, CHIRALITY IND COMMER
[8] AN EQUATION UTILIZING EMPIRICALLY DERIVED SUBSTITUENT CONSTANTS FOR THE PREDICTION OF VICINAL COUPLING-CONSTANTS IN SUBSTITUTED ETHANES
COLUCCI, WJ
JUNGK, SJ
GANDOUR, RD
[J]. MAGNETIC RESONANCE IN CHEMISTRY, 1985, 23 (05) : 335 - 343
[9] CONFORMATIONAL STUDY OF CINCHONA ALKALOIDS - A COMBINED NMR AND MOLECULAR-ORBITAL APPROACH
DIJKSTRA, GDH
KELLOGG, RM
WYNBERG, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) : 6121 - 6131
[10] ELECTRON-ENERGY LOSS AND THERMAL-DESORPTION SPECTROSCOPY OF PYRIDINE ADSORBED ON PT(111)
GRASSIAN, VH
MUETTERTIES, EL
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1986, 90 (22) : 5900 - 5907

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