Enantioselective Catalytic Synthesis ofN-alkylated Indoles

被引：18
|
作者：
Trubitson, Dmitri [1 ]
Kanger, Tonis [1 ]
机构：
[1] Tallinn Univ Technol, Sch Sci, Dept Chem & Biotechnol, Akad Tee 15, EE-12618 Tallinn, Estonia
来源：
SYMMETRY-BASEL | 2020年 / 12卷 / 07期
关键词：
indole; asymmetric synthesis; organocatalysis; transition-metal catalysis; C-N bond formation; enantioselective; heterocycles; FRIEDEL-CRAFTS ALKYLATION; N-ALKYLATION; NITROGEN-HETEROCYCLES; ALLYLIC ALKYLATION; FUNCTIONALIZATION; HYDROAMINATION; DIVERSITY; PYRROLES; CASCADE;
D O I：
10.3390/sym12071184
中图分类号：
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号：
07 ; 0710 ; 09 ;
摘要：
During the past two decades, the interest in new methodologies for the synthesis of chiralN-functionalized indoles has grown rapidly. The review illustrates efficient applications of organocatalytic and organometallic strategies for the construction of chiral alpha-N-branched indoles. Both the direct functionalization of the indole core and indirect methods based on asymmetricN-alkylation of indolines, isatins and 4,7-dihydroindoles are discussed.
引用
收藏
页数：30
相关论文
共 50 条
  • [1] Enantioselective synthesis of indoles through catalytic indolization
    Yang, Bin-Miao
    Ng, Xiao Qian
    Zhao, Yu
    CHEM CATALYSIS, 2022, 2 (11): : 3048 - 3076
  • [2] Catalytic Enantioselective Synthesis of Spirooxindoles by Oxidative Rearrangement of Indoles
    Qian, Chenxiao
    Li, Pengfei
    Sun, Jianwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (11) : 5871 - 5875
  • [3] Enantioselective N-alkylation of isatins and synthesis of chiral N-alkylated indoles
    Dou, Xiaowei
    Yao, Weijun
    Jiang, Chunhui
    Lu, Yixin
    CHEMICAL COMMUNICATIONS, 2014, 50 (77) : 11354 - 11357
  • [4] An update on catalytic enantioselective alkylations of indoles
    Bandini, Marco
    Eichholzer, Astrid
    Umani-Ronchi, Achille
    MINI-REVIEWS IN ORGANIC CHEMISTRY, 2007, 4 (02) : 115 - 124
  • [5] Catalytic Enantioselective Additions of Indoles to Nitroalkenes
    Ganesh, Madhu
    Seidel, Daniel
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (49) : 16464 - +
  • [6] Asymmetric Synthesis of Indolines by Catalytic Enantioselective Reduction of 3H-Indoles
    Rueping, Magnus
    Brinkmann, Claus
    Antonchick, Andrey P.
    Atodiresei, Iuliana
    ORGANIC LETTERS, 2010, 12 (20) : 4604 - 4607
  • [7] Catalytic Enantioselective Synthesis of Atropisomeric Indoles with an N-C Chiral Axis
    Ototake, Nobutaka
    Morimoto, Yudai
    Mokuya, Ayano
    Fukaya, Haruhiko
    Shida, Yasuo
    Kitagawa, Osamu
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (23) : 6752 - 6755
  • [8] Highly enantioselective synthesis of chiral 3-substituted indolines by catalytic asymmetric hydrogenation of indoles
    Kuwano, R
    Kaneda, K
    Ito, T
    Sato, K
    Kurokawa, T
    Ito, Y
    ORGANIC LETTERS, 2004, 6 (13) : 2213 - 2215
  • [9] New strategies for the synthesis of N-alkylated indoles (Review)
    Karchava, A. V.
    Melkonyan, F. S.
    Yurovskaya, M. A.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (03) : 391 - 407
  • [10] New strategies for the synthesis of N-alkylated indoles (Review)
    A. V. Karchava
    F. S. Melkonyan
    M. A. Yurovskaya
    Chemistry of Heterocyclic Compounds, 2012, 48 : 391 - 407
12345