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
[1]   Helix-sense-selective polymerization of phenylacetylene having two hydroxy groups using a chiral catalytic system [J].
Aoki, T ;
Kaneko, T ;
Maruyama, N ;
Sumi, A ;
Takahashi, M ;
Sato, T ;
Teraguchi, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (21) :6346-6347
[2]   α,β-unsaturated 2-acyl imidazoles as a practical class of dienophiles for the DNA-Based catalytic asymmetric diels-alder reaction in water [J].
Boersma, Arnold J. ;
Feringa, Ben L. ;
Roelfes, Gerard .
ORGANIC LETTERS, 2007, 9 (18) :3647-3650
[3]   OPTICALLY-ACTIVE POLYMERS OF 1-ALKYNES [J].
CIARDELLI, F ;
LANZILLO, S ;
PIERONI, O .
MACROMOLECULES, 1974, 7 (02) :174-179
[4]  
Coquiere D., 2007, ANGEW CHEM, V119, P9468
[5]   DNA-Based catalytic enantioselective Michael reactions in water [J].
Coquiere, David ;
Feringa, Ben L. ;
Roelfes, Gerard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (48) :9308-9311
[6]   Chiral architectures from macromolecular building blocks [J].
Cornelissen, JJLM ;
Rowan, AE ;
Nolte, RJM ;
Sommerdijk, NAJM .
CHEMICAL REVIEWS, 2001, 101 (12) :4039-4070
[7]   ENANTIOSELECTIVE POLYMERIZATIONS OF ACHIRAL ISOCYANIDES - PREPARATION OF OPTICALLY-ACTIVE HELICAL POLYMERS USING CHIRAL NICKEL-CATALYSTS [J].
DEMING, TJ ;
NOVAK, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (20) :7926-7927
[8]   The combinatorial synthesis of chiral phosphine ligands [J].
Gilbertson, SR ;
Wang, XF .
TETRAHEDRON LETTERS, 1996, 37 (36) :6475-6478
[9]   A HELICAL POLYMER WITH A COOPERATIVE RESPONSE TO CHIRAL INFORMATION [J].
GREEN, MM ;
PETERSON, NC ;
SATO, T ;
TERAMOTO, A ;
COOK, R ;
LIFSON, S .
SCIENCE, 1995, 268 (5219) :1860-1866
[10]   Asymmetric hydrosilylation of styrenes catalyzed by palladium-MOP complexes: Ligand modification and mechanistic studies [J].
Hayashi, T ;
Hirate, S ;
Kitayama, K ;
Tsuji, H ;
Torii, A ;
Uozumi, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1441-1449