Influence of amphiphile concentration on the enantioselectivity in the rhodium-catalyzed reduction of unsaturated substrates in water

被引：26
作者：
Robert, F
Oehme, G
Grassert, I
Sinou, D
机构：
[1] Univ Lyon 1, CPE Lyon, Lab Synthese Asymetr, F-69622 Villeurbanne, France
[2] Univ Rostock, Inst Organ Katalyseforsch, D-18055 Rostock, Germany
来源：
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2000年 / 156卷 / 1-2期
关键词：
asymmetric hydrogenation; rhodium; surfactants; CMC;
D O I：
10.1016/S1381-1169(99)00422-7
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 enantioselectivity of the asymmetric hydrogenation of some unsaturated amino acid precursors with [Rh(COD)(1)]BF4 and [Rh(COD)(2)]ClO4 as catalyst is influenced by the presence of amphiphiles. Performing the reduction in water, both the activity and the enantioselectivity are enhanced significantly in the presence of surfactants. The determination of the CMC of some surfactants, as well as the reduction in mixtures of water/methanol in the presence of amphiphiles, give some evidence for the importance of micelles formation in these enhancements. (C) 2000 Elsevier Science B.V. All rights reserved.
引用
收藏
页码：127 / 132
页数：6
相关论文
共 22 条
[1]  
[Anonymous], ASYMMETRIC SYNTHESIS
[2]  
Beller M., 1998, TRANSITION METALS OR, V2, P1
[3]  
Bunton CA., 1987, ADV PHYS ORG CHEM, V22, P213, DOI [10.1016/S0065-3160(08)60169-0, DOI 10.1016/S0065-3160(08)60169-0]
[4]  
BUNTON CA, 1991, SURFACTANT SCI SER, V38, P13
[5]  
Dwars T, 1998, ANGEW CHEM INT EDIT, V37, P2851, DOI 10.1002/(SICI)1521-3773(19981102)37:20<2851::AID-ANIE2851>3.0.CO
[6]  
2-F
[7]  
FENDLER JH, 1982, MEMBRANE MIMETIC CHE
[8]   DETERMINING THE CRITICAL MICELLE CONCENTRATION OF AQUEOUS SURFACTANT SOLUTIONS - USING A NOVEL COLORIMETRIC METHOD [J].
FURTON, KG ;
NORELUS, A .
JOURNAL OF CHEMICAL EDUCATION, 1993, 70 (03) :254-257
[9]   Use of rhodium complexes with amphiphilic and nonamphiphilic ligands for the preparation of chiral α-aminophosphonic acid esters by hydrogenation in micellar media [J].
Grassert, I ;
Schmidt, U ;
Ziegler, S ;
Fischer, C ;
Oehme, G .
TETRAHEDRON-ASYMMETRY, 1998, 9 (23) :4193-4202
[10]   Investigation of the influence of carbohydrate amphiphiles on the complex catalysed asymmetric hydrogenation of (Z)-methyl alpha-acetamidocinnamate in water [J].
Grassert, I ;
Vill, V ;
Oehme, G .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 116 (1-2) :231-236
123