Gold Catalysis: Switching the Pathway of the Furan-Yne Cyclization

被引:102
作者
Hashmi, A. Stephen K. [1 ]
Rudolph, Matthias [1 ]
Huck, Juergen [1 ]
Frey, Wolfgang [2 ]
Bats, Jan W. [3 ]
Hamzic, Melissa [1 ]
机构
[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany
[2] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany
[3] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60439 Frankfurt, Germany
关键词
alkynes; arylation; ethers; gold; heterocycles; PHENOL SYNTHESIS; HOMOGENEOUS CATALYSIS; BOND FORMATION; C-C; CYCLOISOMERIZATION; DEAROMATIZATION; COMPLEXES; ALKYNES; ENYNES; TRANSFORMATIONS;
D O I
10.1002/anie.200900887
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Changing tracks: By the use of alkynyl ethers as directing elements, the furan-yne cyclization enters a new reaction pathway. Instead of phenols, tetracycles containing two heteroatoms and two new stereocenters are formed (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5848 / 5852
页数:5
相关论文
共 77 条
  • [1] Gold(I)-catalysed arylation of 1,6-enynes: different site reactivity of cyclopropyl gold carbenes
    Amijs, Catelijne H. M.
    Ferrer, Catalina
    Echavarren, Antonio M.
    [J]. CHEMICAL COMMUNICATIONS, 2007, (07) : 698 - 700
  • [2] [Anonymous], ANGEW CHEM
  • [3] [Anonymous], ANGEW CHEM
  • [4] [Anonymous], 2004, ANGEW CHEM, DOI DOI 10.1002/ANGE.200460232
  • [5] [Anonymous], 2007, ANGEW CHEM
  • [6] Gold catalysis in the reactions of 1,3-dicarbonyls with nucleophiles
    Arcadi, A
    Bianchi, G
    Di Giuseppe, S
    Marinelli, F
    [J]. GREEN CHEMISTRY, 2003, 5 (01) : 64 - 67
  • [7] Alternative synthetic methods through new developments in catalysis by gold
    Arcadi, Antonio
    [J]. CHEMICAL REVIEWS, 2008, 108 (08) : 3266 - 3325
  • [8] Asymmetric dearomatization of the furan ring promoted by conjugate organolithimn addition to (menthyloxy)(3-furyl)carbene complexes of chromium
    Barluenga, J
    Nandy, SK
    Laxmi, YRS
    Suárez, JR
    Merino, I
    Flórez, J
    García-Granda, S
    Montejo-Bernardo, J
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (23) : 5725 - 5736
  • [9] Doubly dearomatising intramolecular coupling of a nucleophilic and an electrophilic heterocycle
    Brice, Heloise
    Clayden, Jonathan
    [J]. CHEMICAL COMMUNICATIONS, 2009, (15) : 1964 - 1966
  • [10] Heterogeneous gold-catalysed synthesis of phenols
    Carrettin, Silvio
    Blanco, M. Carmen
    Corma, Avelino
    Hashmi, A. Stephen K.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (10-11) : 1283 - 1288