Ir-catalysed asymmetric hydrogenation:: Ligands, substrates and mechanism

被引:161
作者
Kallström, K [1 ]
Munslow, I [1 ]
Andersson, PG [1 ]
机构
[1] Uppsala Univ, Kem Inst, Avd F Organisk Kemi, S-75124 Uppsala, Sweden
关键词
asymmetric catalysis; density functional calculations; hydrogenation; iridium; olefins;
D O I
10.1002/chem.200500755
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Relatively air and moisture tolerant cationic iridium complexes, with chiral non-racemic N,P-ligands and weakly coordinating counter ions, are efficient catalysts in the asymmetric hydrogenation of olefins. Unfunctionalised olefins are particularly difficult substrates because, in general, a polar group adjacent to the alkene bond is required for high catalytic activity and enantioselectivity. The applicability towards a variety of substrates and choice of ligands reported thus far in the literature, as well as the mechanism, selectivity issues and the importance of the anion are also discussed.
引用
收藏
页码:3194 / 3200
页数:7
相关论文
共 50 条
[31]   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
[32]   Synthesis and application of chiral phosphino-imidazoline ligands: Ir-catalyzed enantioselective hydrogenation [J].
Menges, F ;
Neuburger, M ;
Pfaltz, A .
ORGANIC LETTERS, 2002, 4 (26) :4713-4716
[33]  
Menges F, 2002, ADV SYNTH CATAL, V344, P40, DOI 10.1002/1615-4169(200201)344:1<40::AID-ADSC40>3.0.CO
[34]  
2-7
[35]  
Noyori R., 1994, ASYMMETRIC CATALYSIS, P16
[36]  
Noyori R., 1994, ASYMMETRIC CATALYSIS
[37]   Optically active iridium imidazol-2-ylidene-oxazoline complexes: Preparation and use in asymmetric hydrogenation of arylalkenes [J].
Perry, MC ;
Cui, XH ;
Powell, MT ;
Hou, DR ;
Reibenspies, JH ;
Burgess, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (01) :113-123
[38]   Iridium-catalyzed enantioselective hydrogenation of olefins [J].
Pfaltz, A ;
Blankenstein, J ;
Hilgraf, R ;
Hörmann, E ;
McIntyre, S ;
Menges, F ;
Schönleber, M ;
Smidt, SP ;
Wüstenberg, B ;
Zimmermann, N .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :33-43
[39]  
PRANDT P, 2003, CHEM-EUR J, V9, P339
[40]   Application of P,N-sulfinyl imine ligands to iridium-catalyzed asymmetric hydrogenation of olefins [J].
Schenkel, LB ;
Ellman, JA .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) :1800-1802