New ruthenium catalysts for asymmetric transfer hydrogenation of prochiral ketones

被引:88
作者
Enthaler, Stephan [1 ]
Hagemann, Bernhard [1 ]
Bhor, Santosh [1 ]
Anilkumar, Gopinathan [1 ]
Tse, Man Kin [1 ]
Bitterlich, Bianca [1 ]
Junge, Kathrin [1 ]
Erre, Giulia [1 ]
Beller, Matthias [1 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
关键词
asymmetric transfer hydrogenation; ketones; phosphines; ruthenium; tridentate nitrogen; ligands;
D O I
10.1002/adsc.200600475
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Tridentate N,N,N-pyridinebisimidazolines have been studied as new ligands for the enantioselective transfer hydrogenation of prochiral ketones. High yields and excellent enantioselectivity up to > 99 % ee have been achieved with an in situ generated catalytic system containing dichlorotris(triphenylphosphine)ruthenium and 2,6-bis-([4R,5R]-4,5diphenyl-4,5-dihydro-1 H-imidazol-2-yl)-pyridine (3a) in the presence of sodium isopropoxide.
引用
收藏
页码:853 / 860
页数:8
相关论文
共 77 条
[1]   Expanding the scope of atropisomeric monodentate P-donor ligands in asymmetric catalysis:: Hydrogen-transfer reduction of α,β-unsaturated acid derivatives by rhodiuni/Ph-binepine catalysts [J].
Alberico, Elisabetta ;
Nieddu, Ilenia ;
Taras, Rossana ;
Gladiali, Serafino .
HELVETICA CHIMICA ACTA, 2006, 89 (08) :1716-1729
[2]   Ruthenium(II)-catalyzed Oppenauer-type oxidation of secondary alcohols [J].
Almeida, MLS ;
Beller, M ;
Wang, GZ ;
Backvall, JE .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (12) :1533-1536
[3]   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
[4]   Synthesis of a novel class of chiral N,N,N-tridentate pyridinebisimidazoline ligands and their application in Ru-catalyzed asymmetric epoxidations [J].
Anilkumar, G ;
Bhor, S ;
Tse, MK ;
Klawonn, M ;
Bitterlich, B ;
Beller, M .
TETRAHEDRON-ASYMMETRY, 2005, 16 (21) :3536-3561
[5]   Evidence for a ruthenium dihydride species as the active catalyst in the RuCl2(PPh3)-catalyzed hydrogen transfer reaction in the presence of base [J].
Aranyos, A ;
Csjernyik, G ;
Szabó, KJ ;
Bäckvall, JE .
CHEMICAL COMMUNICATIONS, 1999, (04) :351-352
[6]   SINGLE ELECTRON-TRANSFER IN THE MEERWEIN-PONNDORF-VERLEY REDUCTION OF BENZOPHENONE BY LITHIUM ALKOXIDES [J].
ASHBY, EC ;
ARGYROPOULOS, JN .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3593-3597
[7]  
Beller M., 2004, Transition Metals for Organic Synthesis, DOI 10.1002/9783527619405
[8]   Svnthesis of a new chiral N,N,N-tridentate pyridinebisimidazoline ligand library and its application in Ru-catalyzed asymmetric epoxidation [J].
Bhor, S ;
Anilkumar, G ;
Tse, MK ;
Klawonn, M ;
Dobler, C ;
Bitterlich, B ;
Grotevendt, A ;
Beller, M .
ORGANIC LETTERS, 2005, 7 (16) :3393-3396
[9]   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
[10]   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