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
[21]   Magnetically recoverable chiral catalysts immobilized on magnetite nanoparticles for asymmetric hydrogenation of aromatic ketones [J].
Hu, AG ;
Yee, GT ;
Lin, WB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (36) :12486-12487
[22]   Remarkable 4,4′-substituent effects on binap:: Highly enantioselective Ru catalysts for asymmetric hydrogenation of β-aryl ketoesters and their immobilization in room-temperature ionic liquids [J].
Hu, AG ;
Ngo, HL ;
Lin, WB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (19) :2501-2504
[23]   Chiral porous hybrid solids for practical heterogeneous asymmetric hydrogenation of aromatic ketones [J].
Hu, AG ;
Ngo, HL ;
Lin, WB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) :11490-11491
[24]   Readily available, recoverable and soluble polymer-monophosphite ligands for highly enantioselective Rh-catalyzed hydrogenation [J].
Hu, XP ;
Huang, JD ;
Zeng, QH ;
Zheng, Z .
CHEMICAL COMMUNICATIONS, 2006, (03) :293-295
[25]   Dendrimers containing chiral ferrocenyl diphosphine ligands for asymmetric catalysis [J].
Köllner, C ;
Pugin, B ;
Togni, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (39) :10274-10275
[26]   Ruthenium catalyzed asymmetric hydrogenation of α- and β-keto esters in ionic liquids using chiral P-Phos ligand [J].
Lam, KH ;
Xu, LJ ;
Feng, LC ;
Ruan, JW ;
Fan, QH ;
Chan, ASC .
CANADIAN JOURNAL OF CHEMISTRY, 2005, 83 (6-7) :903-908
[27]   Asymmetric hydrogenation of ketones with polymer-supported chiral 1,2-diphenylethylenediamine [J].
Li, XG ;
Chen, WP ;
Hems, W ;
King, F ;
Xiao, JL .
ORGANIC LETTERS, 2003, 5 (24) :4559-4561
[28]   Programmed assembly of two different ligands with metallic ions: Generation of self-supported Noyori-type catalysts for heterogeneous asymmetric hydrogenation of ketones [J].
Liang, YX ;
Jing, Q ;
Li, X ;
Shi, L ;
Ding, KL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7694-7695
[29]   Asymmetric hydrogenation of an α,β-unsaturated ketone by diamine(ether-phosphine)ruthenium(II) complexes and lipase-catalyzed kinetic resolution:: a consecutive approach [J].
Lindner, E ;
Ghanem, A ;
Warad, I ;
Eichele, K ;
Mayer, HA ;
Schurig, V .
TETRAHEDRON-ASYMMETRY, 2003, 14 (08) :1045-1053
[30]   Novel dendritic ligands of chiral 1,2-diamine and their application in asymmetric hydrogenation of simple aryl ketones [J].
Liu, WG ;
Cui, X ;
Cun, LF ;
Wu, J ;
Zhu, J ;
Deng, JG ;
Fan, QH .
SYNLETT, 2005, (10) :1591-1595