Chiral [RuCl2(dipyridylphosphane)(1,2-diamine)] catalysts:: Applications in asymmetric hydrogenation of a wide range of simple ketones

被引:115
作者
Wu, J [1 ]
Ji, JX [1 ]
Guo, RW [1 ]
Yeung, CH [1 ]
Chan, ASC [1 ]
机构
[1] Hong Kong Polytech Univ, Inst Mol Technol Drug Discovery & Synth, Open Lab Chirotechnol, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China
关键词
asymmetric catalysis; enantioselectivity; hydrogentation; P ligands; ruthenium;
D O I
10.1002/chem.200204688
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The dipyridylphosphane/diamine-Ru complex combined with tBuOK in 2-propanol acts as a very effective catalyst system for the enantioselective hydrogenation of a diverse range of simple ketones including heteroaromatic ketones, substituted benzophenones, alkenyl ketones, and cyclopropyl ketones. The combination of desirable features, such as quantitative chemical yields within hours, broad substrate scope, excellent enantioselectivities (up to 99%) and high substrate-to-catalyst ratios, among others, makes the present catalyst system of high practical interest.
引用
收藏
页码:2963 / 2968
页数:6
相关论文
共 90 条
[1]   Enzymatic resolution of (R)- and (S)-2-(1-hydroxyalkyl)thiazoles, synthetic equivalents of (R)- and (S)-2-hydroxy aldehydes [J].
Allevi, P ;
Ciuffreda, P ;
Tarocco, G ;
Anastasia, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (12) :4144-4147
[2]   Ru(arene)(amino alcohol)-catalyzed transfer hydrogenation of ketones: Mechanism and origin of enantioselectivity [J].
Alonso, DA ;
Brandt, P ;
Nordin, SJM ;
Andersson, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9580-9588
[3]  
[Anonymous], 1998, ANGEW CHEM, V110, P1792
[4]   ASYMMETRIC REDUCTION WITH CHIRAL ORGANOBORANES BASED ON ALPHA-PINENE [J].
BROWN, HC ;
RAMACHANDRAN, PV .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (01) :16-24
[5]   EFFECTIVE ASYMMETRIC HYDROBORATION CATALYZED BY A RHODIUM COMPLEX OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE [J].
BROWN, JM ;
HULMES, DI ;
LAYZELL, TP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (22) :1673-1674
[6]   ASYMMETRIC SYNTHESES .20. ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH [RH(COD)CL]2 THIAZOLIDINE CATALYSTS [J].
BRUNNER, H ;
BECKER, R ;
RIEPL, G .
ORGANOMETALLICS, 1984, 3 (09) :1354-1359
[7]   Asymmetric catalytic routes to chiral building blocks of medicinal interest [J].
Burk, MJ ;
Gross, MF ;
Harper, TGP ;
Kalberg, CS ;
Lee, JR ;
Martinez, JP .
PURE AND APPLIED CHEMISTRY, 1996, 68 (01) :37-44
[8]   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
[9]   Chiral synthesis via organoboranes.: 46.: An efficient preparation of chiral pyridino- and thiopheno-18-crown-6 ligands from enantiomerically pure C2-symmetric pyridine- and thiophenediols [J].
Chen, GM ;
Brown, HC ;
Ramachandran, PV .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :721-725
[10]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO