Cobalt(I) Catalysis in the Diastereoselective Two-Step Synthesis of Tricyclic Systems

被引:4
作者
Erver, Florian [1 ]
Hilt, Gerhard [1 ]
Harms, Klaus [1 ]
机构
[1] Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany
来源
SYNTHESIS-STUTTGART | 2011年 / 06期
关键词
alkyne; catalysis; cobalt; cycloaddition; diene; multicomponent reaction; hetero-Diels-Alder reaction; DIELS-ALDER REACTIONS; 2+2+2 CYCLOADDITION; ORGANIC-SYNTHESIS; BENZENE-DERIVATIVES; ALKYNES;
D O I
10.1055/s-0030-1258433
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The diastereoselective two-step synthesis of heterotricyclic systems is accomplished by regioselective cobalt-catalysed [4+2]- and [4+2+2]-cycloaddition reactions generating cyclohexa-1,4-diene and cycloocta-1,3,6-triene derivatives, and a hetero-Diels-Alder reaction. Thus, a set of selected cyclohexadienes and cyclooctatrienes were reacted with cyclic 1,3-diones and formaldehyde in a Knoevenagel-hetero-Diels-Alder multicomponent reaction to produce a variety of tricyclic products.
引用
收藏
页码:972 / 978
页数:7
相关论文
共 23 条
  • [1] Ambient-Temperature Cobalt-Catalyzed Cycloaddition Strategies to Aromatic Boronic Esters
    Auvinet, Anne-Laure
    Harrity, Joseph P. A.
    Hilt, Gerhard
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (11) : 3893 - 3896
  • [2] DANZ M, 2011, ADV SYNTH C IN PRESS
  • [3] Beyond Reppe: Building Substituted Arenes by [2+2+2] Cycloadditions of Alkynes
    Galan, Brandon R.
    Rovis, Tomislav
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) : 2830 - 2834
  • [4] Cobalt-Catalysed Carbon-Carbon Bond-Formation Reactions
    Hess, Wilfried
    Treutwein, Jonas
    Hilt, Gerhard
    [J]. SYNTHESIS-STUTTGART, 2008, (22): : 3537 - 3562
  • [5] Regioselective cobalt-catalyzed Diels-Alder reaction towards 1,3-disubstituted and 1,2,3-trisubstituted benzene derivatives
    Hilt, Gerhard
    Danz, Michael
    [J]. SYNTHESIS-STUTTGART, 2008, (14): : 2257 - 2263
  • [6] Cobalt-catalyzed [4+2+2] cycloaddition for the synthesis of 1,3,6-cyclooctatrienes
    Hilt, Gerhard
    Janikowski, Judith
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (28) : 5243 - 5245
  • [7] Cobalt-catalyzed intermolecular [2+2+2] cycloaddition for the synthesis of 1,3-cyclohexadienes
    Hilt, Gerhard
    Paul, Anna
    Harms, Klaus
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13) : 5187 - 5190
  • [8] Cobalt-catalyzed [2+2+2] cycloaddition of phenylacetylene with 1,3-dienes for the synthesis of Vinyl-substituted 1,4-diphenylcyclohexa-1,3-dienes
    Hilt, Gerhard
    Hess, Wilfried
    Harms, Klaus
    [J]. SYNTHESIS-STUTTGART, 2008, 1 (01): : 75 - 78
  • [9] meta-directing cobalt-catalyzed Diels-Alder reactions
    Hilt, Gerhard
    Janikowski, Judith
    Hess, Wilfried
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (31) : 5204 - 5206
  • [10] Cobalt-Catalyzed Generation of 1,4-Dienes as Synthons for 1,3-Dicarbonyl Compounds and Their Application in Natural Product Syntheses
    Hilt, Gerhard
    Arndt, Marion
    Weske, Damian F.
    [J]. SYNTHESIS-STUTTGART, 2010, (08): : 1321 - 1324