Enantioselective Friedel-Crafts Alkylation of N-Methylindoles with Nitroalkenes Catalyzed by Chiral Bifunctional Abietic-Acid-Derived Thiourea-ZnII Complexes

被引：18
作者：
Huang, Wei-gen [1 ]
Wang, Heng-shan [1 ]
Huang, Guo-bao [1 ]
Wu, Yong-ming [1 ]
Pan, Ying-ming [1 ]
机构：
[1] Guangxi Normal Univ, Key Lab Chem & Mol Engn Med Resources, Minist Educ China, Sch Chem & Chem Engn, Guilin 541004, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 29期
关键词：
Asymmetric synthesis; C-C coupling; Friedel-Crafts alkylation; Zinc; Aromatic substitution; Nitroalkenes; CONJUGATE ADDITION; MICHAEL ADDITION; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; INDOLES; DERIVATIVES; ORGANOCATALYSTS; RECOGNITION; SEPARATIONS; LIGAND;
D O I：
10.1002/ejoc.201200584
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The catalytic asymmetric FriedelCrafts alkylation of N-methylindoles with nitroalkenes catalyzed by bifunctional abietic-acid-derived thiourea-ZnII complexes was investigated. Various types of the nitroalkylated indoles were synthesized under mild conditions and obtained with excellent yields (up to 99?%) and good enantioselectivities (up to 86?%?ee). These chiral thiourea catalysts are easily available from the commercial abietic acid.
引用
收藏
页码：5839 / 5843
页数：5
相关论文
共 51 条
  • [1] [Anonymous], 2004, ANGEW CHEM-GER EDIT
  • [2] Asymmetric Catalytic Cycloetherification Mediated by Bifunctional Organocatalysts
    Asano, Keisuke
    Matsubara, Seijiro
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (42) : 16711 - 16713
  • [3] New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction
    Bandini, M
    Melloni, A
    Umani-Ronchi, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) : 550 - 556
  • [4] Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
  • [5] Dual Catalysis in Enantioselective Oxidopyrylium-Based [5+2] Cycloadditions
    Burns, Noah Z.
    Witten, Michael R.
    Jacobsen, Eric N.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (37) : 14578 - 14581
  • [6] Organocatalysis mediated by (thio)urea derivatives
    Connon, Stephen J.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (21) : 5418 - 5427
  • [7] Small-molecule H-bond donors in asymmetric catalysis
    Doyle, Abigail G.
    Jacobsen, Eric N.
    [J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5713 - 5743
  • [8] Marine natural products
    Faulkner, DJ
    [J]. NATURAL PRODUCT REPORTS, 2001, 18 (01) : 1 - 49
  • [9] Novel axially chiral bis-arylthiourea-based organocatalysts for asymmetric Friedel-Crafts type reactions
    Fleming, Eimear M.
    McCabe, Thomas
    Connon, Stephen J.
    [J]. TETRAHEDRON LETTERS, 2006, 47 (39) : 7037 - 7042
  • [10] Catalytic Enantioselective Additions of Indoles to Nitroalkenes
    Ganesh, Madhu
    Seidel, Daniel
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (49) : 16464 - +
123456