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
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 14期
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
  • [1] [Anonymous], COMPREHENSIVE HETERO
  • [2] [Anonymous], 2003, CHEM HETEROCYCLES ST, DOI DOI 10.1002/352760183X
  • [3] Highly efficient access to strained bicyclic ketals via gold-catalyzed cycloisomerization of bis-homopropargylic diols
    Antoniotti, S
    Genin, E
    Michelet, V
    Genêt, JP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) : 9976 - 9977
  • [4] An Extremely Facile Synthesis of Furans, Pyrroles, and Thiophenes by the Dehydrative Cyclization of Propargyl Alcohols
    Aponick, Aaron
    Li, Chuan-Ying
    Malinge, Jeremy
    Marques, Emerson Finco
    [J]. ORGANIC LETTERS, 2009, 11 (20) : 4624 - 4627
  • [5] Alternative synthetic methods through new developments in catalysis by gold
    Arcadi, Antonio
    [J]. CHEMICAL REVIEWS, 2008, 108 (08) : 3266 - 3325
  • [6] Gold-catalyzed tandem cycloisomerization-hydroalkoxylation of homopropargylic alcohols
    Belting, Volker
    Krause, Norbert
    [J]. ORGANIC LETTERS, 2006, 8 (20) : 4489 - 4492
  • [7] Blunt J.W., 2006, Nat. Prod. Rep, V17, P235
  • [8] Gold(I)-catalyzed reactions: substituents-dependent selective formation of bisfurans and 1,3-diketones from 1-allkynyl-2,3-epoxy alcohols
    Dai, Lun-Zhi
    Shi, Min
    [J]. TETRAHEDRON LETTERS, 2008, 49 (45) : 6437 - 6439
  • [9] DEAN F.M., 1963, NATURALLY OCCURRING
  • [10] DEAN FM, 1982, ADV HETEROCYCL CHEM, V31, P237
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