Fast and highly regioselective allylation of indole and pyrrole compounds by allyl alcohols using Ru-sulfonate catalysts

被引：81
作者：
Zaitsev, Alexey B. [1 ]
Gruber, Stefan [1 ]
Pluess, Pascal A. [1 ]
Pregosin, Paul S. [1 ]
Veiros, Luis F. [2 ]
Woerle, Michael [1 ]
机构：
[1] ETHZ, Inorgan Chem Lab, CH-8093 Zurich, Switzerland
[2] Univ Tecn Lisboa, Ctr Quim Estrutural, Inst Super Tecn, P-1049001 Lisbon, Portugal
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 35期
基金：
瑞士国家科学基金会;
关键词：
D O I：
10.1021/ja804379k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
New Ru-sulfonate catalysts have been synthesized and shown to very rapidly allylate indole and pyrrole compounds using allyl alcohols as substrates. The observed regioselectivity is exceptionally high (up to 100% of the branched isomer). Density functional theory calculations explain these results.
引用
收藏
页码：11604 / +
页数：3
相关论文
共 19 条
  • [1] New versatile Pd-catalyzed alkylation of indoles via nucleophilic allylic subsitution: Controlling the regioselectivity
    Bandini, M
    Melloni, A
    Umani-Ronchi, A
    [J]. ORGANIC LETTERS, 2004, 6 (18) : 3199 - 3202
  • [2] Palladium-catalysed cross-coupling and related reactions involving pyrroles
    Banwell, Martin G.
    Goodwin, Thomas E.
    Ng, Sarah
    Smith, Jason A.
    Wong, David J.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (14) : 3043 - 3060
  • [3] Enantioselective Pd-catalyzed allylic alkylation of Indoles by a new class of chiral ferrocenyl P/S Ligands
    Cheung, Hong Yee
    Yu, Wing-Yiu
    Lam, Fuk Loi
    Au-Yeung, Terry T. -L.
    Zhou, Zhongyuan
    Chan, Tak Hang
    Chan, Albert S. C.
    [J]. ORGANIC LETTERS, 2007, 9 (21) : 4295 - 4298
  • [4] Lamellarins and related pyrrole-derived alkaloids from marine organisms
    Fan, Hui
    Peng, Jiangnan
    Hamann, Mark T.
    Hu, Jin-Feng
    [J]. CHEMICAL REVIEWS, 2008, 108 (01) : 264 - 287
  • [5] High-yield ruthenium-catalyzed Friedel-Crafts type allylation reactions using dicationic RuIV catalysts
    Fernandez, Ignacio
    Hermatschweiler, Rene
    Breher, Frank
    Pregosin, Paul S.
    Veiros, Luis F.
    Calhorda, Maria Jose
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (38) : 6386 - 6391
  • [6] Frisch M.J., 2004, Gaussian 03
  • [7] Revision C.02
  • [8] Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents
    Galliford, Chris V.
    Scheidt, Karl A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) : 8748 - 8758
  • [9] Indole alkaloid marine natural products: An established source of cancer drug leads with considerable promise for the control of parasitic, neurological and other diseases
    Gul, W
    Hamann, MT
    [J]. LIFE SCIENCES, 2005, 78 (05) : 442 - 453
  • [10] Kimura M, 2006, HETEROCYCLES, V67, P535
12