Copper-catalyzed dimerization of chromium Fischer carbene complexes:: synthesis of dialkoxytrienes and their Nazarov-type cyclization to 2-alkoxy-2-cyclopentenones

被引:28
作者
Barluenga, J [1 ]
Barrio, P [1 ]
Vicente, R [1 ]
López, LA [1 ]
Tomás, M [1 ]
机构
[1] Univ Oviedo, CSIC, Unidad Asociada, Inst Univ Quim Organomet Enrique Moles, E-33006 Oviedo, Spain
关键词
chromium carbenes; copper(I) carbenes; carbene transfer; dimerization; 2-cyclopentenone; Nazarov reaction;
D O I
10.1016/j.jorganchem.2004.07.005
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Fischer carbene complexes 1 underwent a clean ligand dimerization reaction yielding functionalized olefins and trienes 4 in the presence of copper (1) catalysts. If treated with trifluoroacetic acid (TFA), trienes 4c, d, f undergo a cyclization process (Nazarov reaction) which furnishes cyclopentenone derivatives 6c, d, 7c, d and 8 in good yields. Finally, the Fischer aminocarbene 9 efficiently cyclodimerizes to the substituted arene 10 in the presence of CuBr. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:3793 / 3799
页数:7
相关论文
共 33 条
  • [1] Catalytic asymmetric nazarov reactions promoted by chiral Lewis acid complexes
    Aggarwal, VK
    Beffield, AJ
    [J]. ORGANIC LETTERS, 2003, 5 (26) : 5075 - 5078
  • [2] Albéniz AC, 2002, ANGEW CHEM INT EDIT, V41, P2363, DOI 10.1002/1521-3773(20020703)41:13<2363::AID-ANIE2363>3.0.CO
  • [3] 2-9
  • [4] Alcaide B, 1998, CURR ORG CHEM, V2, P551
  • [5] Aumann R, 2000, EUR J ORG CHEM, V2000, P17, DOI 10.1002/(SICI)1099-0690(200001)2000:1<17::AID-EJOC17>3.0.CO
  • [6] 2-T
  • [7] Aumann R, 1999, EUR J ORG CHEM, V1999, P2545
  • [8] Metal-controlled selective [3+2] cyclization reactions of alkenyl Fischer carbene complexes and allenes
    Barluenga, J
    Vicente, R
    Barrio, P
    López, LA
    Tomás, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) : 5974 - 5975
  • [9] New Fischer carbene complexes of rhodium(I):: Preparation and 2-cyclopentenone ring synthesis by annelation to alkynes
    Barluenga, J
    Vicente, R
    López, LA
    Rubio, E
    Tomás, M
    Alvarez-Rúa, C
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (02) : 470 - 471
  • [10] Nickel(0)-mediated [3+2+2] and [2+2+2+1] cyclization reactions of chromium Fischer carbene complexes and alkynes
    Barluenga, J
    Barrio, P
    López, LA
    Tomás, M
    García-Granda, S
    Alvarez-Rúa, C
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (26) : 3008 - 3011