Catalytic reduction of acetophenone with transition metal systems containing chiral bis(oxazolines)

被引:21
|
作者
Gómez, M
Jansat, S
Muller, G
Bonnet, MC
Breuzard, JAJ
Lemaire, M
机构
[1] Univ Lyon 1, UMR 5622, Lab Catalyse & Synthese Organ, F-69622 Villeurbanne, France
[2] Univ Barcelona, Dept Quim Inorgan, E-08028 Barcelona, Spain
关键词
homogenous catalysis; chiral bis(oxazolines); transition metals; NMR spectroscopy; PM3(tm) calculations;
D O I
10.1016/S0022-328X(02)01767-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The catalytic behaviour of several Ru, Rh and It systems containing bis(oxazoline) ligands (1-6) has been tested in the asymmetric reduction of acetophenone (7) to give 1-phenylethanol (8) by hydrogenation (Ir systems), transfer hydrogenation (It and Ru systems) and hydrosilylation (Ir and Rh systems). Ligands 1 and 3 gave good activities, obtaining the best asymmetric induction with Ir-1 system in the hydrosilylation (ee up to 50% (S) of 8). In order to identify the catalytic precursors, Ru (9-11) and It (12) complexes were synthesised and characterised. NMR studies of ruthenium complexes showed the existence of two main isomers in a ca. ratio 3/1, in agreement with the PM3(tm) calculations carried out for 10. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:186 / 195
页数:10
相关论文
共 50 条
  • [1] The chiral metal complexes of pyridine-2,6-bis(oxazolines) and their applications in catalytic asymmetric reactions
    Zhong, Liqin
    Tang, Ruiren
    Yang, Qing
    [J]. PROGRESS IN CHEMISTRY, 2007, 19 (06) : 902 - 910
  • [2] BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS
    EVANS, DA
    WOERPEL, KA
    HINMAN, MM
    FAUL, MM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) : 726 - 728
  • [3] Recent advances in the immobilization of chiral catalysts containing bis(oxazolines) and related ligands
    Fraile, Jose M.
    Garcia, Jose I.
    Mayoral, Jose A.
    [J]. COORDINATION CHEMISTRY REVIEWS, 2008, 252 (5-7) : 624 - 646
  • [4] Palladium complexes containing bis(oxazolines):: stoichiometric versus catalytic allylic alkylation
    Gómez, M
    Jansat, S
    Muller, G
    Maestro, MA
    Saavedra, JM
    Font-Bardía, M
    Solans, X
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2001, (09): : 1432 - 1439
  • [5] Synthesis of two new chiral fluorous bis(oxazolines) and their applications as ligands in catalytic asymmetric reactions
    Bayardon, J
    Sinou, D
    [J]. TETRAHEDRON-ASYMMETRY, 2005, 16 (17) : 2965 - 2972
  • [6] Sulfur-containing chiral bis(oxazolines) tested in copper-catalyzed asymmetric cyclopropanation
    Gao, MZ
    Wang, B
    Kong, DY
    Zingaro, RA
    Clearfield, A
    Xu, ZL
    [J]. SYNTHETIC COMMUNICATIONS, 2005, 35 (20) : 2665 - 2673
  • [7] Cationic ring opening cyclopolymerization of bis(oxazolines). Synthesis of chiral polymers containing pendent heteromacrocycles
    Puts, RD
    Sogah, DY
    [J]. MACROMOLECULES, 1997, 30 (22) : 6826 - 6836
  • [8] Optically active transition metal compounds containing chiral transition metal atoms
    Brunner, H
    [J]. CHEMICAL SYNTHESIS: GNOSIS TO PROGNOSIS, 1996, 320 : 91 - 111
  • [9] Catalytic reduction of NOx over transition-metal-containing MCM-41
    Schiesser, W
    Vinek, H
    Jentys, A
    [J]. CATALYSIS LETTERS, 1998, 56 (04) : 189 - 194
  • [10] Catalytic reduction of NOx over transition-metal-containing MCM-41
    Walter Schießer
    Hannelore Vinek
    Andreas Jentys
    [J]. Catalysis Letters, 1998, 56 : 189 - 194