Iridium-catalyzed asymmetric hydrogenation of olefins

被引:505
作者
Roseblade, Stephen J. [1 ]
Pfaltz, Andreas [1 ]
机构
[1] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland
关键词
D O I
10.1021/ar700113g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric hydrogenation is one of the most important catalytic methods for the preparation of optically active compounds. For a long time the range of olefins that could be hydrogenated with high enantiomeric excess was limited to substrates bearing a coordinating group next to the C=C bond. We have found a new class of catalysts, iridium complexes with chiral P, N ligands, that overcome these limitations. For a wide range Of unfunctionalized olefins, excellent enantioselectivities could be achieved. Because these catalysts do not require the presence of any particular functional group in the substrate, they considerably broaden the scope of asymmetric hydrogenation. In addition, promising results were also obtained with certain functionalized alkenes, furans, and benzofurans.
引用
收藏
页码:1402 / 1411
页数:10
相关论文
共 66 条
[41]   Synthesis of a new class of conformationally rigid phosphino-oxazolines: Highly enantioselective ligands for Ir-catalyzed asymmetric hydrogenation [J].
Liu, D ;
Tang, WJ ;
Zhang, X .
ORGANIC LETTERS, 2004, 6 (04) :513-516
[42]   Synthesis of tunable phosphinite-pyridine ligands and their applications in asymmetric hydrogenation [J].
Liu, Qi-Bin ;
Yu, Chang-Bin ;
Zhou, Yong-Gui .
TETRAHEDRON LETTERS, 2006, 47 (27) :4733-4736
[43]   A combined experimental and computational study of dihydrido(phosphinooxazoline)iridium complexes [J].
Mazet, C ;
Smiidt, SP ;
Meuwly, M ;
Pfaltz, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (43) :14176-14181
[44]   Iridium-catalyzed enantioselective hydrogenation of terminal alkenes [J].
McIntyre, S ;
Hörmann, E ;
Menges, F ;
Smidt, SP ;
Pfaltz, A .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) :282-288
[45]  
Menges F, 2002, ADV SYNTH CATAL, V344, P40, DOI 10.1002/1615-4169(200201)344:1<40::AID-ADSC40>3.0.CO
[46]  
2-7
[47]  
MENGES F, 2004, THESIS U BASEL
[48]   Diphenylphosphanylsulfoximines as ligands in iridium-catalyzed asymmetric imine hydrogenations [J].
Moessner, C ;
Bolm, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (46) :7564-7567
[49]  
Noyori R, 2002, ANGEW CHEM INT EDIT, V41, P2008, DOI 10.1002/1521-3773(20020617)41:12<2008::AID-ANIE2008>3.0.CO
[50]  
2-4