Iridium catalysts for the asymmetric hydrogenation of olefins with nontraditional functional substituents

被引:210
作者
Church, Tamara L. [1 ]
Andersson, Pher G. [1 ]
机构
[1] Uppsala Univ, Dept Biochem & Organ Chem, S-75123 Uppsala, Sweden
关键词
asymmetric hydrogenation; iridium catalysts; functionalized olefins; non-coordinating olefins;
D O I
10.1016/j.ccr.2007.09.015
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Chiral iridium catalysts have now been used in the asymmetric hydrogenation of largely unfunctionallized olefins for a decade. Recently, they have also been applied to substrates with more exotic functional groups, including non-coordinating ones. These, unlike coordinating substituents, cannot direct asymmetric hydrogenation by rhodium- or ruthenium-based catalysts. This review discusses several classes of these less familiar substrates, outlines the progress that has been made toward their stereoselective hydrogenation, and highlights the role of iridium complexes in this emerging field. We hope this will inspire researchers to consider iridium-catalyzed asymmetric hydrogenation as a potential route to a broad range of chiral compounds. (c) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:513 / 531
页数:19
相关论文
共 187 条
[21]   PREPARATION AND PROPERTIES OF CHIRAL FLUOROORGANIC COMPOUNDS [J].
BRAVO, P ;
RESNATI, G .
TETRAHEDRON-ASYMMETRY, 1990, 1 (10) :661-692
[22]   ASYMMETRIC HYDROGENATION OF UNFUNCTIONALIZED TRISUBSTITUTED OLEFINS WITH A CHIRAL TITANOCENE CATALYST [J].
BROENE, RD ;
BUCHWALD, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) :12569-12570
[23]  
BROWN JM, COMPREHENSIVE ASYMME, V1
[24]  
Brunel J.M., 2003, Rec. Res. Dev. Org. Chem, V7, P155
[25]  
Brunner H, 2000, MONATSH CHEM, V131, P1371, DOI 10.1007/s007060070017
[26]   Stereoselective synthesis of the antifungal GM222712 [J].
Bueno, JM ;
Coterón, JM ;
Chiara, JL ;
Fernández-Mayoralas, A ;
Fiandor, JM ;
Valle, N .
TETRAHEDRON LETTERS, 2000, 41 (22) :4379-4382
[27]   Synthesis of piperidines [J].
Buffat, MGP .
TETRAHEDRON, 2004, 60 (08) :1701-1729
[28]   C2-SYMMETRICAL BIS(PHOSPHOLANES) AND THEIR USE IN HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].
BURK, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8518-8519
[29]   NEW ELECTRON-RICH CHIRAL PHOSPHINES FOR ASYMMETRIC CATALYSIS [J].
BURK, MJ ;
FEASTER, JE ;
HARLOW, RL .
ORGANOMETALLICS, 1990, 9 (10) :2653-2655
[30]   Enantioselective synthesis of α-hydroxy and α-amino phosphonates via catalytic asymmetric hydrogenation [J].
Burk, MJ ;
Stammers, TA ;
Straub, JA .
ORGANIC LETTERS, 1999, 1 (03) :387-390