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
[1]   Recent applications of chiral ferrocene ligands in asymmetric catalysis [J].
Arrayas, Ramon Gomez ;
Adrio, Javier ;
Carretero, Juan Carlos .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (46) :7674-7715
[2]   KINETICS AND MECHANISM OF CATALYSIS OF THE ASYMMETRIC HYDROGENATION OF ALPHA-BETA-UNSATURATED CARBOXYLIC-ACIDS BY BIS(CARBOXYLATO)(2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL)-RUTHENIUM(II), [RUII(BINAP)(O2CR)2] [J].
ASHBY, MT ;
HALPERN, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :589-594
[3]  
Bains W, 2003, CURR OPIN DRUG DISC, V6, P526
[4]   Aromaticity as a cornerstone of heterocyclic chemistry [J].
Balaban, AT ;
Oniciu, DC ;
Katritzky, AR .
CHEMICAL REVIEWS, 2004, 104 (05) :2777-2812
[5]   Synthesis of Chiraphos via asymmetric hydrogenation of 2,3-bis(diphenylphosphinoyl)buta-1,3-diene [J].
Beghetto, V ;
Matteoli, U ;
Scrivanti, A .
CHEMICAL COMMUNICATIONS, 2000, (02) :155-156
[6]   Asymmetric hydrogenation of unfunctionalized, purely alkyl-substituted olefins [J].
Bell, S ;
Wüstenberg, B ;
Kaiser, S ;
Menges, F ;
Netscher, T ;
Pfaltz, A .
SCIENCE, 2006, 311 (5761) :642-644
[7]   Transition metal complexes with the C1-symmetric diphosphines (R)-(R)-3-benzyl-2,4-bis(diphenylphosphino)pentane and (R)-(R)-3-benzyl(p-sulphonate)-2,4-bis(diphenylphosphino)pentane sodium salt.: Applications to enantioselective catalysis in different phase systems [J].
Bianchini, C ;
Barbaro, P ;
Scapacci, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 621 (1-2) :26-33
[8]   Enantioselective hydrogenation of 2-methylquinoxaline to (-)-(2S)-2-methyl-1,2,3,4-tetrahydroquinoxaline by iridium catalysis [J].
Bianchini, C ;
Barbaro, P ;
Scapacci, G ;
Farnetti, E ;
Graziani, M .
ORGANOMETALLICS, 1998, 17 (15) :3308-3310
[9]   HETEROAROMATICITY .5. A UNIFIED AROMATICITY INDEX [J].
BIRD, CW .
TETRAHEDRON, 1992, 48 (02) :335-340
[10]  
Blackmond DG, 2000, CHIRALITY, V12, P442, DOI 10.1002/(SICI)1520-636X(2000)12:5/6<442::AID-CHIR25>3.0.CO