Immobilization of asymmetric multifunctional catalysts on an insoluble polymer

被引:76
作者
Matsunaga, S [1 ]
Ohshima, T [1 ]
Shibasaki, M [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
基金
日本学术振兴会;
关键词
asymmetric catalyst; asymmetric synthesis; solid-phase synthesis; Michael reaction; linked-BINOL;
D O I
10.1016/S0040-4039(00)01486-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Polymer-supported linked-BINOL was synthesized to immobilize asymmetric catalysts with two BINOL units. The advantage of the polymer-supported linked-BINOL over randomly polymer-supported BINOL was confirmed by asymmetric Michael reaction. A novel polymer-supported La-Zn-linked-BINOL complex afforded the Michael adduct in good yield and moderate ee. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8473 / 8478
页数:6
相关论文
共 19 条
  • [1] Polymer-supported chiral Co(salen) complexes: Synthetic applications and mechanistic investigations in the hydrolytic kinetic resolution of terminal epoxides
    Annis, DA
    Jacobsen, EN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) : 4147 - 4154
  • [2] Preparation and use of a polymer supported BINAP hydrogenation catalyst
    Bayston, DJ
    Fraser, JL
    Ashton, MR
    Baxter, AD
    Polywka, MEC
    Moses, E
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) : 3137 - 3140
  • [3] Palladium diaqua and hydroxo complexes with polymer-supported BINAP ligands and their use for catalytic enantioselective reactions
    Fujii, A
    Sodeoka, M
    [J]. TETRAHEDRON LETTERS, 1999, 40 (45) : 8011 - 8014
  • [4] Heckel A, 2000, ANGEW CHEM INT EDIT, V39, P163, DOI 10.1002/(SICI)1521-3773(20000103)39:1<163::AID-ANIE163>3.0.CO
  • [5] 2-J
  • [6] Development of highly enantioselective polymeric catalysts using rigid and sterically regular chiral polybinaphthols
    Huang, WS
    Hu, QS
    Zheng, XF
    Anderson, J
    Pu, L
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (18) : 4313 - 4314
  • [7] Hetero-dinuclear metal complexes for RNA hydrolysis
    Kamitani, J
    Kawahara, R
    Yashiro, M
    Komiyama, M
    [J]. CHEMISTRY LETTERS, 1998, (10) : 1047 - 1048
  • [8] Stable, storable, and reusable asymmetric catalyst: A novel La-linked-BINOL complex for the catalytic asymmetric Michael reaction
    Kim, YS
    Matsunaga, S
    Das, J
    Sekine, A
    Ohshima, T
    Shibasaki, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (27) : 6506 - 6507
  • [9] Chiral catalyst optimization using both solid-phase and liquid-phase methods in asymmetric aza Diels-Alder reactions
    Kobayashi, S
    Kusakabe, K
    Ishitani, H
    [J]. ORGANIC LETTERS, 2000, 2 (09) : 1225 - 1227
  • [10] Catalytic enantioselective meso-epoxide ring opening reaction with phenolic oxygen nucleophile promoted by gallium heterobimetallic multifunctional complexes
    Matsunaga, S
    Das, J
    Roels, J
    Vogl, EM
    Yamamoto, N
    Iida, T
    Yamaguchi, K
    Shibasaki, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) : 2252 - 2260