Polymerisation vs. grafting in the preparation of polymer-supported aluminium catalysts for the Diels-Alder reaction:: The role of the polymeric backbone.

被引:29
作者
Altava, B [1 ]
Burguete, MI [1 ]
García-Verdugo, E [1 ]
Luis, SV [1 ]
Salvador, RV [1 ]
Vicent, MJ [1 ]
机构
[1] Univ Jaume 1, Dept Inorgan & Organ Chem, ESTCE, E-12080 Castellon de La Plana, Spain
关键词
asymmetric induction; catalysis; Diels-Alder reactions; polymeric support;
D O I
10.1016/S0040-4020(99)00763-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several polymers containing Al Lewis acids anchored to chiral prolinol moieties have been prepared and studied as catalyst for the Diels-Alder reaction of cyclopentadiene and methacrolein. The chiral fragment has been introduced by grafting and by polymerisation procedures using different crosslinking agents and ratios. All supported catalysts prepared show a good activity, but the polymeric network seems to play it very important role in the determining the selectivity observed. Best results, in terms of enantioselectivity. are obtained when the chiral fragment is introduced through polymerisation of the appropriate chiral monomer, but only when a high crosslinking degree (90% DVB) is used. It is shown that the presence of coordinating atoms in the polymeric backbone is clearly detrimental for the selectivity observed. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:12897 / 12906
页数:10
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  • [1] APPLICATION OF FUNCTIONALIZED POLYMERS IN ORGANIC-SYNTHESIS
    AKELAH, A
    SHERRINGTON, DC
    [J]. CHEMICAL REVIEWS, 1981, 81 (06) : 557 - 587
  • [2] Altava B, 1997, STUD SURF SCI CATAL, V108, P509
  • [3] Altava B, 1997, AN QUIM, V93, P260
  • [4] Polymer-grafted Ti-TADDOL complexes. Preparation and use as catalysts in Diels-Alder reactions
    Altava, B
    Burguete, MI
    Escuder, B
    Luis, SV
    Salvador, RV
    Fraile, JM
    Mayoral, JA
    Royo, AJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) : 3126 - 3134
  • [5] ALTAVA B, IN PRESS EUR J ORG C
  • [6] 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
  • [7] Balkenhohl F, 1996, ANGEW CHEM INT EDIT, V35, P2289
  • [8] Synthesis and evaluation of a chiral heterogeneous transfer hydrogenation catalyst
    Bayston, DJ
    Travers, CB
    Polywka, MEC
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (12) : 2015 - 2018
  • [9] Blossey E. C., 1989, COMPREHENSIVE POLYM, V6, P81
  • [10] Bolm C, 1998, EUR J ORG CHEM, V1998, P21, DOI 10.1002/(SICI)1099-0690(199801)1998:1<21::AID-EJOC21>3.0.CO