Site-isolated base- and acid-mediated Michael-initiated cyclization cascades

被引:62
作者
Pilling, Adam W.
Boehmer, Jutta
Dixon, Darren J.
机构
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
[2] Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England
关键词
cascade reactions; cyclization; iminium ions; Michael addition; N-ACYLIMINIUM IONS; ONE-POT REACTIONS; OPPOSING REAGENTS; ORGANIC CATALYSTS; ENZYME;
D O I
10.1002/anie.200701079
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) One thing leads to another: Site-isolated base and acid catalysts have been exploited in Michael addition, N-acyl iminium ion cyclization cascades with amide pronucleophiles and α,β- unsaturated carbonyl compounds. The reaction sequence has broad scope, uses commercially available catalysts, is atom efficient, and can be scaled by way of a flow-reactor setup. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5428 / 5430
页数:3
相关论文
共 27 条
  • [1] Polymer-supported organic catalysts
    Benaglia, M
    Puglisi, A
    Cozzi, F
    [J]. CHEMICAL REVIEWS, 2003, 103 (09) : 3401 - 3429
  • [2] ORGANIC-SYNTHESIS INVOLVING MULTI-POLYMER REACTIONS - POLYMERIC TRITYLLITHIUM
    COHEN, BJ
    KRAUS, MA
    PATCHORNIK, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (12) : 4165 - 4167
  • [3] Immobilization of organic catalysts: When, why, and how
    Cozzi, Franco
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (12-13) : 1367 - 1390
  • [4] One-pot sequences of reactions with sol-gel entrapped opposing reagents: An enzyme and metal-complex catalysts
    Gelman, F
    Blum, J
    Avnir, D
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (48) : 14460 - 14463
  • [5] One-pot reactions with opposing reagents: Sol-gel entrapped catalyst and base
    Gelman, F
    Blum, J
    Avnir, D
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) : 11999 - 12000
  • [6] Gelman F, 2001, ANGEW CHEM INT EDIT, V40, P3647, DOI 10.1002/1521-3773(20011001)40:19<3647::AID-ANIE3647>3.0.CO
  • [7] 2-A
  • [8] Gelman F., 2001, ANGEW CHEM, V113, P3759
  • [9] Multipolymer solution-phase reactions: Application to the Mitsunobu reaction
    Harned, AM
    He, HS
    Toy, PH
    Flynn, DL
    Hanson, PR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) : 52 - 53
  • [10] One-pot reaction cascades using star polymers with core-confined catalysts
    Helms, B
    Guillaudeu, SJ
    Xie, Y
    McMurdo, M
    Hawker, CJ
    Fréchet, JMJ
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (39) : 6384 - 6387