Gold-catalyzed cyclization of enyne-1,6-diols to substituted furans

被引:25
作者
Kim, Sundae [1 ,2 ]
Kang, Dongjin [1 ,2 ]
Shin, Seunghoon [3 ]
Lee, Phil Ho [1 ,2 ]
机构
[1] Kangwon Natl Univ, Dept Chem, Natl Res Lab Catalyt Organ React, Chunchon 200701, South Korea
[2] Kangwon Natl Univ, Inst Mol Sci & Fus Technol, Chunchon 200701, South Korea
[3] Hanyang Univ, Dept Chem, Seoul 133791, South Korea
关键词
TANDEM CYCLOISOMERIZATION; EFFICIENT SYNTHESIS; C-C; KETONES; NUCLEOPHILES; GOLD(III); ALCOHOLS; ALLENES; ALKYNES; RINGS;
D O I
10.1016/j.tetlet.2010.02.026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of enyne-1,6-diols with 5 mol % Ph3PAuCl in the presence of 5 mol % AgOTf as a cocatalyst selectively produced trisubstituted furans in good to excellent yields in dichloromethane at room temperature for 5-10 min through cyclization followed by isomerization. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1899 / 1901
页数:3
相关论文
共 54 条
  • [11] Dyker G, 2000, ANGEW CHEM INT EDIT, V39, P4237, DOI 10.1002/1521-3773(20001201)39:23<4237::AID-ANIE4237>3.0.CO
  • [12] 2-A
  • [13] Strategy and methodology development for the total synthesis of polyether ionophore antibiotics
    Faul, MM
    Huff, BE
    [J]. CHEMICAL REVIEWS, 2000, 100 (06) : 2407 - 2473
  • [14] Fernandez J.J., 2000, Nat. Prod. Rep, V23, P26
  • [15] EFFECTIVE TRANSFORMATION OF UNACTIVATED ALKYNES INTO KETONES OR ACETALS BY MEANS OF AU(III) CATALYST
    FUKUDA, Y
    UTIMOTO, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) : 3729 - 3731
  • [16] Relativistic effects in homogeneous gold catalysis
    Gorin, David J.
    Toste, F. Dean
    [J]. NATURE, 2007, 446 (7134) : 395 - 403
  • [17] Gold-catalyzed organic reactions
    Hashmi, A. Stephen K.
    [J]. CHEMICAL REVIEWS, 2007, 107 (07) : 3180 - 3211
  • [18] Gold catalysis
    Hashmi, A. Stephen K.
    Hutchings, Graham J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (47) : 7896 - 7936
  • [19] Gold catalysis in total synthesis
    Hashmi, A. Stephen K.
    Rudolph, Matthias
    [J]. CHEMICAL SOCIETY REVIEWS, 2008, 37 (09) : 1766 - 1775
  • [20] Hashmi ASK, 2000, ANGEW CHEM INT EDIT, V39, P2285, DOI 10.1002/1521-3773(20000703)39:13<2285::AID-ANIE2285>3.0.CO