Recent Progress in the Construction of Chiral 3-Substituted Indoles by Asymmetric Friedel-Crafts Reactions

被引:0
|
作者
Liu Tiantian [1 ]
Duan Xinhong [1 ]
机构
[1] Beijing Forestry Univ, Coll Sci, Beijing 100083, Peoples R China
关键词
chiral catalyst; asymmetric Friedel-Crafts alkylation; C(3)-substituted chiral indole; chiral induction; DIELS-ALDER REACTION; ENANTIOSELECTIVE SYNTHESIS; PHOSPHORIC-ACID; MICHAEL ADDITION; ALKYLATION REACTIONS; HETEROAROMATIC-COMPOUNDS; HIGHLY EFFICIENT; DIRECT ARYLATION; BRONSTED ACIDS; CARBONYL-ENE;
D O I
10.6023/cjoc202303010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral C(3)-functionalized indoles have received much attention as strategic building blocks for the synthesis of many natural products and bioactive compounds. Particularly in the past twenty years, application of chiral metal complexes and small-molecule organocatalysts for the asymmetric Friedel-Crafts C(3)-alkylations of indoles has become a hot topic in the organic field. Applications of asymmetric Friedel-Crafts reactions in the synthesis of C(3)-substituted indoles are reviewed according to the catalysts that promoting reaction. Moreover, future perspectives are also presented.
引用
收藏
页码:3695 / 3712
页数:18
相关论文
共 143 条
  • [1] Stronger bronsted acids
    Akiyama, Takahiko
    [J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5744 - 5758
  • [2] Stronger Bronsted Acids: Recent Progress
    Akiyama, Takahiko
    Mori, Keiji
    [J]. CHEMICAL REVIEWS, 2015, 115 (17) : 9277 - 9306
  • [3] Recent progress in chiral Bronsted acid catalysis
    Akiyama, Takahiko
    Itoh, Junji
    Fuchibe, Kohei
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) : 999 - 1010
  • [4] Enantioselective H-Bond-Directing Approach for Trienamine-mediated Reactions in Asymmetric Synthesis
    Albrecht, Lukasz
    Acosta, Fabio Cruz
    Fraile, Alberto
    Albrecht, Anna
    Christensen, Jannie
    Jorgensen, Karl Anker
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) : 9088 - 9092
  • [5] Asymmetric Organocatalytic Formal [2+2]-Cycloadditions via Bifunctional H-Bond Directing Dienamine Catalysis
    Albrecht, Lukasz
    Dickmeiss, Gustav
    Acosta, Fabio Cruz
    Rodriguez-Escrich, Carles
    Davis, Rebecca L.
    Jorgensen, Karl Anker
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (05) : 2543 - 2546
  • [6] Squaramides: Bridging from Molecular Recognition to Bifunctional Organocatalysis
    Aleman, Jose
    Parra, Alejandro
    Jiang, Hao
    Jorgensen, Karl Anker
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (25) : 6890 - 6899
  • [7] Switchable reactivity of acylated α,β-dehydroamino ester in the Friedel-Crafts alkylation of indoles by changing the Lewis acid
    Angelini, Elena
    Balsamini, Cesarino
    Bartoccini, Francesca
    Lucarini, Simone
    Piersanti, Giovanni
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14): : 5654 - 5657
  • [8] Origins of the Stereoselectivity in a Thiourea-Primary Amine-Catalyzed Nazarov Cyclization
    Asari, Austin H.
    Lam, Yu-hong
    Tius, Marcus A.
    Houk, K. N.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (40) : 13191 - 13199
  • [9] 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
  • [10] Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple α,β-unsaturated ketones
    Bartoli, Giuseppe
    Bosco, Marcella
    Carlone, Armando
    Pesciaioli, Fabio
    Sambri, Letizia
    Melchiorre, Paolo
    [J]. ORGANIC LETTERS, 2007, 9 (07) : 1403 - 1405