Gold-Catalyzed Cycloisomerizations of 1,n-Diyne Carbonates and Esters

被引:147
作者
Day, David Philip [1 ]
Chan, Philip Wai Hong [1 ,2 ]
机构
[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England
[2] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia
基金
澳大利亚研究理事会;
关键词
alkynes; cyclization; gold; homogeneous catalysis; synthetic methods; HIGHLY EFFICIENT SYNTHESIS; PROPARGYLIC ESTERS; GOLD(I)-CATALYZED CYCLOISOMERIZATION; INTERMOLECULAR HYDROAMINATION; 1,6-DIYNE CARBONATES; PLATINUM CATALYSIS; DUAL-ACTIVATION; CYCLIZATION; ALKYNE; ACCESS;
D O I
10.1002/adsc.201600005
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Driven by the ever-growing need for efficient methods to prepare synthetically valuable complex molecules, homogeneous gold catalysis has emerged as an invaluable addition in the organic chemist's toolbox to achieve such goals. Within this field of catalysis, this review focuses on the contributions made toward the construction of core structural scaffolds found in bioactive natural products and pharmaceutical compounds from gold-catalyzed reactions of 1,n-diyne carbonates and esters. It covers the advances made through exploiting the reactivity of the substrate class triggered by an initial 1,2- or 1,3-acyloxy migration of the propargyl motif as well as one rare example of a concerted double cyclization pathway.
引用
收藏
页码:1368 / 1384
页数:17
相关论文
共 107 条
  • [1] Carbocyclisation of alkynes with external nucleophiles catalysed by gold, platinum and other electrophilic metals
    Abu Sohel, Shariar Md.
    Liu, Rai-Shung
    [J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) : 2269 - 2281
  • [2] [Anonymous], 2013, ANGEW CHEM, V125, P2653
  • [3] [Anonymous], ANGEW CHEM
  • [4] [Anonymous], 2012, ANGEW CHEM
  • [5] Harnessing the Versatile Reactivity of Propargyl Alcohols and their Derivatives for Sustainable Complex Molecule Synthesis
    Ayers, Benjamin James
    Chan, Philip Wai Hong
    [J]. SYNLETT, 2015, 26 (10) : 1305 - 1339
  • [6] On the Impact of Steric and Electronic Properties of Ligands on Gold(I)-Catalyzed Cycloaddition Reactions
    Benitez, Diego
    Tkatchouk, Ekaterina
    Gonzalez, Ana Z.
    Goddard, William A., III
    Toste, F. Dean
    [J]. ORGANIC LETTERS, 2009, 11 (21) : 4798 - 4801
  • [7] Gold Catalysis 2.0
    Braun, Ingo
    Asiri, Abdullah Mohamed
    Hashmi, A. Stephen K.
    [J]. ACS CATALYSIS, 2013, 3 (08): : 1902 - 1907
  • [8] Gold-catalyzed cascade cycloisomerization of 1,7-diyn-3,6-bis(propargyl carbonate)s: stereoselective synthesis of naphtho[b]cyclobutenes
    Chen, Ming
    Liu, Jun
    Wang, Lu
    Zhou, Xiaobo
    Liu, Yuanhong
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (77) : 8650 - 8652
  • [9] Chen Y., 2012, ANGEW CHEM, V124, P6599
  • [10] Gold-Catalyzed Cascade Cyclizations of 1,6-Diynyl Carbonates to Benzo[b]fluorenes Involving Arylation of Oxocarbenium Ion Intermediates and Decarboxylative Etherification
    Chen, Yifeng
    Chen, Ming
    Liu, Yuanhong
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (26) : 6493 - 6497