Gold(I)-catalyzed 5-endo hydroxy- and alkoxycyclization of 1,5-enynes:: Efficient access to functionalized cyclopentenes

被引:128
作者
Buzas, Andrea K. [1 ]
Istrate, Florin M. [1 ]
Gagosz, Fabien [1 ]
机构
[1] Ecole Polytech, Organ Synth Lab, CNRS, UMR 7652, F-91128 Palaiseau, France
关键词
C-C coupling; cyclization; cyclopentenes; gold; metathesis;
D O I
10.1002/anie.200604140
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) The rapid and stereoselective construction of highly functionalized cyclopentenes is possible through gold(I)-catalyzed 5-endo hydroxy- and methoxycyclizations of 1,5-enynes. More complex 5,7-and 5,8-fused bicyclic structures of a type found in many terpene natural products can be formed by combining the cyclization reaction with ring-closing metathesis (RCM; see scheme). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1141 / 1144
页数:4
相关论文
共 43 条
  • [21] 4745::AID-ANGE4745ANDGT
  • [22] 3.0.CO
  • [23] 2-S
  • [24] Ligand effects in gold- and platinum-catalyzed cyclization of enynes:: Chiral gold complexes for enantioselective alkoxycyclization
    Muñoz, MP
    Adrio, J
    Carretero, JC
    Echavarren, AM
    [J]. ORGANOMETALLICS, 2005, 24 (06) : 1293 - 1300
  • [25] MUNOZMP, 2003, SYNTHESIS, P2898
  • [26] Gold(I)-catalyzed cyclizations of 1,6-enynes:: Alkoxycyclizations and exo/endo skeletal rearrangements
    Nieto-Oberhuber, C
    Muñoz, MP
    López, S
    Jiménez-Núñer, E
    Nevado, C
    Herrero-Gómez, E
    Raducan, M
    Echavarren, AM
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (06) : 1677 - 1693
  • [27] Divergent mechanisms for the skeletal rearrangement and [2+2] cycloaddition of enynes catalyzed by gold
    Nieto-Oberhuber, C
    López, S
    Muñoz, MP
    Cárdenas, DJ
    Buñuel, E
    Nevado, C
    Echavarren, AM
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) : 6146 - 6148
  • [28] Intramolecular [4+2] cycloadditions of 1,3-enynes or arylalkynes with alkenes with highly reactive cationic phosphine Au(I) complexes
    Nieto-Oberhuber, C
    López, S
    Echavarren, AM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) : 6178 - 6179
  • [29] Nieto-Oberhuber C., 2005, ANGEW CHEM, V117, P6302
  • [30] Gold(l)-catalyzed propargyl Claisen rearrangement
    Sherry, BD
    Toste, FD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (49) : 15978 - 15979