Asymmetric Hydrogenation of Ketones with H2 and Ruthenium Catalysts Containing Chiral Tetradentate S2N2 Ligands

被引:52
作者
Patchett, Ruth [1 ]
Magpantay, Iris [1 ]
Saudan, Lionel [1 ]
Schotes, Christoph [2 ]
Mezzetti, Antonio [2 ]
Santoro, Francesco [1 ]
机构
[1] Firmenich Co, Corp R&D Div, CH-1211 Geneva 8, Switzerland
[2] ETH, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland
关键词
alcohols; asymmetric hydrogenation; homogeneous catalysis; ruthenium; S ligands; ENANTIOSELECTIVE HYDROGENATION; STEREOSELECTIVE HYDROGENATION; SELECTIVE HYDROGENATION; COMPLEXES; PHOSPHORUS; SULFUR;
D O I
10.1002/anie.201304844
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Getting more for less: In the presence of H2 and a base, air- and moisture-tolerant RuII complexes catalyze the hydrogenation of ketones and aldehydes with excellent activity and chemoselectivity, and with enantioselectivity of up to 95 % under mild conditions. The ratio of substrate to catalyst can be lowered to 106:1. The reactions tolerate scale-up and can be carried out with almost no solvent. A base-free method is available for base-sensitive substrates. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:10352 / 10355
页数:4
相关论文
共 47 条
[1]  
[Anonymous], 2008, ANGEW CHEM, V120, P954, DOI DOI 10.1002/ANGE.200705115
[2]  
[Anonymous], 2002, [No title captured], Patent No. [WO 2002040155 A1, 2002040155]
[3]   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
[4]  
Doucet H, 1998, ANGEW CHEM INT EDIT, V37, P1703, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1703::AID-ANIE1703>3.0.CO
[5]  
2-I
[6]  
Doucet H., 1998, ANGEW CHEM, V110, P1792
[7]   Ruthenium-Catalyzed Selective Hydrogenation for Flavor and Fragrance Applications [J].
Dupau, Philippe .
ORGANOMETALLICS AS CATALYSTS IN THE FINE CHEMICAL INDUSTRY, 2012, 42 :47-63
[8]  
Elsevier C.J, 2006, HDB HOMOGENEOUS HYDR
[9]   A ruthenium(II) complex with a C-2-symmetric diphosphine/diamine tetradentate ligand for asymmetric transfer hydrogenation of aromatic ketones [J].
Gao, JX ;
Ikariya, T ;
Noyori, R .
ORGANOMETALLICS, 1996, 15 (04) :1087-1089
[10]   PNS-Type Ruthenium Pincer Complexes [J].
Gargir, Moti ;
Ben-David, Yehoshua ;
Leitus, Gregory ;
Diskin-Posner, Yael ;
Shimon, Linda J. W. ;
Milstein, David .
ORGANOMETALLICS, 2012, 31 (17) :6207-6214