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.

引用

页码：2573 / 2577

页数：5

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