Asymmetric transfer hydrogenation in water with a supported Noyori-Ikariya catalyst

被引:177
作者
Li, XG
Wu, XF
Chen, WP
Hancock, FE
King, F
Xiao, JL [1 ]
机构
[1] Univ Liverpool, Dept Chem, Liverpool Ctr Mat & Catalysis, Liverpool L69 7ZD, Merseyside, England
[2] Johnson Matthey, Billingham TS23 1LB, Cleveland, England
关键词
D O I
10.1021/ol0487175
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The poly(ethylene glycol)-supported ruthenium precatalyst shown above is highly effective for asymmetric transfer hydrogenation of unfunctionalized aromatic ketones by HCOONa in neat water, affording fast rates, good to excellent enantioselectivities, and outstanding reusability.
引用
收藏
页码:3321 / 3324
页数:4
相关论文
共 52 条
[1]   Synthesis and evaluation of a chiral heterogeneous transfer hydrogenation catalyst [J].
Bayston, DJ ;
Travers, CB ;
Polywka, MEC .
TETRAHEDRON-ASYMMETRY, 1998, 9 (12) :2015-2018
[2]   Selective hydrogenation for fine chemicals: Recent trends and new developments [J].
Blaser, HU ;
Malan, C ;
Pugin, B ;
Spindler, F ;
Steiner, H ;
Studer, M .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :103-151
[3]   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
[4]   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
[5]   Kinetic isotope effect evidence for a concerted hydrogen transfer mechanism in transfer Hydrogenations catalyzed by [p-(Me2CH)C6H4Me]Ru-(NHCHPhCHPhNSO2C6H4-p-CH3) [J].
Casey, CP ;
Johnson, JB .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1998-2001
[6]   Dendritic catalysts for asymmetric transfer hydrogenation [J].
Chen, YC ;
Wu, TF ;
Deng, JG ;
Liu, H ;
Jiang, YZ ;
Choib, MCK ;
Chan, ASC .
CHEMICAL COMMUNICATIONS, 2001, (16) :1488-1489
[7]   Soluble polymers as scaffolds for recoverable catalysts and reagents [J].
Dickerson, TJ ;
Reed, NN ;
Janda, KD .
CHEMICAL REVIEWS, 2002, 102 (10) :3325-3343
[8]   Rutheuium(II)-catalyzed asymmetric transfer hydrogenation of carbonyl compounds with 2-propanol and ephedrine-type ligands [J].
Everaere, K ;
Mortreux, A ;
Carpentier, JF .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :67-77
[9]   Recoverable catalysts for asymmetric organic synthesis [J].
Fan, QH ;
Li, YM ;
Chan, ASC .
CHEMICAL REVIEWS, 2002, 102 (10) :3385-3465
[10]   Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture [J].
Fujii, A ;
Hashiguchi, S ;
Uematsu, N ;
Ikariya, T ;
Noyori, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2521-2522