β-amino alcohols as ligands for asymmetric transfer hydrogenation of ketones in water

被引:57
作者
Wu, XF [1 ]
Li, XH [1 ]
McConville, M [1 ]
Saidi, O [1 ]
Xiao, JL [1 ]
机构
[1] Univ Liverpool, Dept Chem, Liverpool Ctr Mat & Catalysis, Liverpool L69 7ZD, Merseyside, England
关键词
asymmetric transfer hydrogenation; beta-amino alcohols; formate; water; pH;
D O I
10.1016/j.molcata.2005.11.040
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
Chiral beta-amino alcohols were used as ligands for ruthenium, rhodium and iridium-catalyzed asymmetric transfer hydrogenation of acetophenones in water with formate as reductant. The catalysts were showed to be capable of asymmetric transfer hydrogenation of ketones in water, but their activities and enantioselectivi ties varied with the ligands used and with Solution pH values, with higher pH favouring higher rates and better enanti oselectivities. (c) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:153 / 158
页数:6
相关论文
共 74 条
[1]   (1S,3R,4R)-2-azanorbornylmethanol, an efficient ligand for ruthenium-catalyzed asymmetric transfer hydrogenation of ketones [J].
Alonso, DA ;
Guijarro, D ;
Pinho, P ;
Temme, O ;
Andersson, PG .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2749-2751
[2]   2-(Aminomethyl)pyridine-phosphine ruthenium(II) complexes: Novel highly active transfer hydrogenation catalysts [J].
Baratta, W ;
Herdtweck, E ;
Siega, K ;
Toniutti, M ;
Rigo, P .
ORGANOMETALLICS, 2005, 24 (07) :1660-1669
[3]  
BLACKER AJ, 1998, Patent No. 9842643
[4]  
BLACKER J, 2002, Patent No. 6372931
[5]  
Blacker J., 2004, ASYMMETRIC CATALYSIS
[6]   Origin of enantioselectivity in the Ru(arene)(amino alcohol)-catalyzed transfer hydrogenation of ketones [J].
Brandt, P ;
Roth, P ;
Andersson, PG .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :4885-4890
[7]   Synthesis of water-soluble aminosulfonamide ligands and their application in enantioselective transfer hydrogenation [J].
Bubert, C ;
Blacker, J ;
Brown, SM ;
Crosby, J ;
Fitzjohn, S ;
Muxworthy, JP ;
Thorpe, T ;
Williams, JMJ .
TETRAHEDRON LETTERS, 2001, 42 (24) :4037-4039
[8]   Synthesis of dendritic catalysts and application in asymmetric transfer hydrogenation [J].
Chen, YC ;
Wu, TF ;
Jiang, L ;
Deng, JG ;
Liu, H ;
Zhu, J ;
Jiang, YZ .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (03) :1006-1010
[9]   Tethered Ru(II) catalysts for asymmetric transfer hydrogenation of ketones [J].
Cheung, FK ;
Hayes, AM ;
Hannedouche, J ;
Yim, ASY ;
Wills, M .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3188-3197
[10]   Mechanisms of the H2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexes [J].
Clapham, SE ;
Hadzovic, A ;
Morris, RH .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2201-2237