An update on catalytic enantioselective alkylations of indoles

被引:20
作者
Bandini, Marco [1 ]
Eichholzer, Astrid [1 ]
Umani-Ronchi, Achille [1 ]
机构
[1] Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
关键词
alkylation; asymmetric catalysis; Friedel-Crafts; indoles;
D O I
10.2174/157019307780599270
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Indole benzylic stereocenters are molecular frameworks largely present in natural occurring compounds, with their absolute configuration being of key importance in determining the biological activity of the entire molecule. In this context, the development of new catalytic asymmetric strategies for their preparation is a research area of astonishingly, rapid growth by means of organic as well as organometallic catalysts. Here, an update of this thriving scenario is presented by focusing in highly stereocontrolled Michael addition approaches, addition to carbonyl units, direct aromatic C-H activation/alkylation, and allylic alkylation.
引用
收藏
页码:115 / 124
页数:10
相关论文
共 50 条
  • [31] Enantioselective N-H Functionalization of Indoles with α,β-Unsaturated γ-Lactams Catalyzed by Chiral Bronsted Acids
    Xie, Yinjun
    Zhao, Yingwei
    Qian, Bo
    Yang, Lei
    Xia, Chungu
    Huang, Hanmin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (25) : 5681 - 5685
  • [32] Catalytic enantioselective addition of diethylzinc to (hetero)aromatic aldehydes
    Lovel, I
    Oehme, G
    Lukevics, E
    APPLIED ORGANOMETALLIC CHEMISTRY, 1998, 12 (07) : 469 - 474
  • [33] Highly Enantioselective Zinc-Catalyzed Friedel-Crafts Alkylation of Indoles with Ethyl Trifluoropyruvate
    Hui, Yonghai
    Chen, Weiliang
    Wang, Wentao
    Jiang, Jun
    Cai, Yunfei
    Lin, Lili
    Liu, Xiaohua
    Feng, Xiaoming
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) : 3174 - 3178
  • [34] Enantioselective Friedel-Crafts Alkylation of Furans and Indoles with Simple α,β-Unsaturated Ketones Catalyzed by Oxazaborolidinone
    Adachi, Shinya
    Tanaka, Fumi
    Watanabe, Kazuya
    Watada, Atsushi
    Harada, Toshiro
    SYNTHESIS-STUTTGART, 2010, (15): : 2652 - 2669
  • [35] Enantioselective Gold-Catalyzed Allylic Alkylation of Indoles with Alcohols: An Efficient Route to Functionalized Tetrahydrocarbazoles
    Bandini, Marco
    Eichholzer, Astrid
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (50) : 9533 - 9537
  • [36] Ruthenium-Catalyzed Enantioselective Propargylation of Indoles with Propargylic Alcohols
    Kanao, Keiichiro
    Matsuzawa, Hiroshi
    Miyake, Yoshihiro
    Nishibayashi, Yoshiaki
    SYNTHESIS-STUTTGART, 2008, (23): : 3869 - 3873
  • [37] Enantioselective Borylative Dearomatization of Indoles through Copper(I) Catalysis
    Kubota, Koji
    Hayama, Keiichi
    Iwamoto, Hiroaki
    Ito, Hajime
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (30) : 8809 - 8813
  • [38] Enantioselective Synthesis of Substituted Indoles Through Zirconium(IV)-Catalyzed Friedel-Crafts Alkylation
    Blay, Gonzalo
    Fernandez, Isabel
    Pedro, Jose R.
    Vila, Carlos
    SYNTHESIS-STUTTGART, 2012, 44 (23): : 3590 - 3594
  • [39] Enantioselective Copper-Catalyzed Dearomative Spiroannulation of β-Naphthols or Indoles with Yne-Allylic Esters
    Zhao, Ruinan
    Deng, Shuang
    Huang, Rongkang
    Kong, Han-Han
    Lu, Yuepeng
    Yin, Tingrui
    Wang, Jiaqiang
    Li, Ying
    Zhu, Cuiju
    Pan, Fangfang
    Qi, Xiaotian
    Xu, Hao
    ACS CATALYSIS, 2024, 14 (12): : 9254 - 9264
  • [40] Organocatalytic enantioselective functionalization of indoles in the carbocyclic ring with cyclic imines
    Vila, Carlos
    Tortosa, Arturo
    Blay, Gonzalo
    Carmen Munoz, M.
    Pedro, Jose R.
    NEW JOURNAL OF CHEMISTRY, 2019, 43 (01) : 130 - 134