Helical Poly(quinoxaline-2,3-diyl)s Bearing Metal-Binding Sites as Polymer-Based Chiral Ligands for Asymmetric Catalysis

被引:170
作者
Yamamoto, Takeshi [1 ]
Suginome, Michinori [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Synthet Chem & Biol Chem, Nishikyo Ku, Kyoto 6158510, Japan
关键词
asymmetric catalysis; block copolymers; chiral ligands; helical structures; hydrosilylation; SENSE-SELECTIVE POLYMERIZATION; OPTICALLY-ACTIVE POLYMERS; SCREW-SENSE; MACROMOLECULAR HELICITY; MEDIATED POLYMERIZATION; ACHIRAL ISOCYANIDES; COMPLEXES; 1,2-DIISOCYANOBENZENES; CONFORMATION; WATER;
D O I
10.1002/anie.200803719
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Living it up: Helical polyquinoxalines with single and multiple metal-binding sites, prepared by living polymerization of o-diisocyanobenzenes, are used in the asymmetric hydrosilylation of styrenes, resulting in comparable enantioselectivities to those obtained by low-molecular-weight catalyst systems (up to 87% ee, stereochemistry was determined by a chiral initiator) and a turnover number of almost 1000. (Chemical Equation Presented). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:539 / 542
页数:4
相关论文
共 41 条
[31]   DNA-based asymmetric catalysis [J].
Roelfes, G ;
Feringa, BL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (21) :3230-3232
[32]  
Roelfes G., 2005, ANGEW CHEM, V117, P3294
[33]   Synthesis of Ru-coordinating helical polymer and its utilization as a catalyst for asymmetric hydrogen-transfer reaction [J].
Sanda, F ;
Araki, H ;
Masuda, T .
CHEMISTRY LETTERS, 2005, 34 (12) :1642-1643
[34]   Trapped kinetic states, chiral amplification and molecular chaperoning in synthetic polymers: Chiral induction in polyguanidines through ion pair interactions [J].
Schlitzer, DS ;
Novak, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (09) :2196-2197
[35]   Transition metal-mediated polymerization of isocyanides [J].
Suginome, M ;
Ito, Y .
POLYMER SYNTHESIS, 2004, 171 :77-136
[36]   Highly effective, easily accessible screw-sense-determining end group in the asymmetric polymerization of 1,2-diisocyanobenzenes [J].
Suginome, M ;
Collet, S ;
Ito, Y .
ORGANIC LETTERS, 2002, 4 (03) :351-354
[37]   Stable helical polyguanidines:: Poly{N-(1-anthryl)-N′-[(R)- and/or (S)-3,7-dimethyloctyl]guanidines} [J].
Tang, HZ ;
Lu, YJ ;
Tian, GL ;
Capracotta, MD ;
Novak, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) :3722-3723
[38]   Helix-sense selective polymerization of carbodiimides: Building permanently optically active polymers from achiral monomers [J].
Tian, GL ;
Lu, YJ ;
Novak, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4082-4083
[39]   CATALYTIC ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE 2-ALKANOLS VIA HYDROSILYLATION OF 1-ALKENES WITH A CHIRAL MONOPHOSPHINE PALLADIUM CATALYST [J].
UOZUMI, Y ;
HAYASHI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) :9887-9888
[40]   Stereospecific deoxygenation of phosphine oxides with retention of configuration using triphenylphosphine or triethyl phosphite as an oxygen acceptor [J].
Wu, HC ;
Yu, JQ ;
Spencer, JB .
ORGANIC LETTERS, 2004, 6 (25) :4675-4678