Asymmetric hydrogenation of α,β-unsaturated ketones catalyzed by Ru-TPPTS-(S,S)-DPENDS complex in ionic liquids

被引:22
作者
Wang, Jinbo
Qin, Ruixiang
Fu, Haiyan
Chen, Jun
Feng, Jian
Chen, Hua
Lia, Xianjun
机构
[1] Sichuan Univ, Coll Chem, Inst Homogeneous Catalysis, Minist Educ,Key Lab Green Chem & Technol, Chengdu 610064, Sichuan, Peoples R China
[2] Weifang Sci & Technol Coll, Coll Chem Engn, Weifang, Peoples R China
关键词
D O I
10.1016/j.tetasy.2007.03.021
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The asymmetric hydrogenation of alpha,beta-unsaturated ketones catalyzed by the achiral ruthenium monophosphine complex RuCl2(TPPTS)(2) [TPPTS: P(m-C6H4SO3Na)(3)] modified by (S,S)-DPENDS [disodium salt of sulfonated (S,S)-1,2-diphenyl-1,2-ethylene-diamine] was investigated in ionic liquid [RMIM]Ts (1-alkyl-3-methytimidazolium p-methylphenylsulfonates, R = ethyl, butyl, octyl, dodecyl). Chemoselectivity of 100% and 75.9% ee were obtained for benzalacetone under the optimized conditions. The resulting products can be easily separated from the catalyst immobilized in ionic liquid [EMIM]Ts by extraction with n-hexane, while the catalyst can be reused seven times without the loss of catalytic activity and enantio selectivity. Especially, the addition of water can improve the performance of the catalyst. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:847 / 851
页数:5
相关论文
共 54 条
[1]   Ionic liquids and chirality: opportunities and challenges [J].
Baudequin, C ;
Baudoux, J ;
Levillain, J ;
Cahard, D ;
Gaumont, AC ;
Plaquevent, JC .
TETRAHEDRON-ASYMMETRY, 2003, 14 (20) :3081-3093
[2]   Preparation and use of a polymer supported BINAP hydrogenation catalyst [J].
Bayston, DJ ;
Fraser, JL ;
Ashton, MR ;
Baxter, AD ;
Polywka, MEC ;
Moses, E .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :3137-3140
[3]   Ionic liquid-phase asymmetric catalytic hydrogenation: hydrogen concentration effects on enantioselectivity [J].
Berger, A ;
de Souza, RF ;
Delgado, MR ;
Dupont, J .
TETRAHEDRON-ASYMMETRY, 2001, 12 (13) :1825-1828
[4]   Enantioselective catalytic asymmetric hydrogenation of ethyl acetoacetate in room temperature ionic liquids [J].
Berthod, M ;
Joerger, JM ;
Mignani, G ;
Vaultier, M ;
Lemaire, M .
TETRAHEDRON-ASYMMETRY, 2004, 15 (14) :2219-2221
[5]  
BONBOTE P, 1996, INORG CHEM, V35, P1168
[6]   Asymmetric hydrogenation and catalyst recycling using ionic liquid and supercritical carbon dioxide [J].
Brown, RA ;
Pollet, P ;
McKoon, E ;
Eckert, CA ;
Liotta, CL ;
Jessop, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (06) :1254-1255
[7]   A catalyst for efficient and highly enantioselective hydrogenation of aromatic, heteroaromatic, and α,β-unsaturated ketones [J].
Burk, MJ ;
Hems, W ;
Herzberg, D ;
Malan, C ;
Zanotti-Gerosa, A .
ORGANIC LETTERS, 2000, 2 (26) :4173-4176
[8]  
CHEN H, 1999, THESIS SICHUAN U
[9]   Dendronized poly(Ru-BINAP) complexes: Highly effective and easily recyclable catalysts for asymmetric hydrogenation [J].
Deng, GJ ;
Yi, B ;
Huang, YY ;
Tang, WJ ;
He, YM ;
Fan, QH .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (12) :1440-1444
[10]  
Doucet H, 1998, ANGEW CHEM INT EDIT, V37, P1703, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1703::AID-ANIE1703>3.0.CO