Enantioselective Friedel-Crafts alkylation for synthesis of 2-substituted indole derivatives

被引:66
|
作者
Zhang, Yulong [1 ]
Liu, Xiaohua [1 ]
Zhao, Xiaohu [1 ]
Zhang, Jianlin [1 ]
Zhou, Lin [1 ]
Lin, Lili [1 ]
Feng, Xiaoming [1 ]
机构
[1] Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China
基金
中国国家自然科学基金;
关键词
CHIRAL BRONSTED ACIDS; ASYMMETRIC-SYNTHESIS; 4,7-DIHYDROINDOLES; CYCLIZATION; CASCADE; PYRROLOINDOLINES; ANNULATION; ALKALOIDS; CATALYSIS; ESTERS;
D O I
10.1039/c3cc45665j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient catalytic asymmetric intermolecular C2 Friedel-Crafts alkylation reaction between N-methyl skatole and beta,gamma-unsaturated alpha-ketoesters has been realized by a chiral N,N'-dioxide-Ni(II) complex. The corresponding indole derivatives were obtained in good yield (up to 96%) with excellent enantioselectivities (up to 99% ee) under mild reaction conditions.
引用
收藏
页码:11311 / 11313
页数:3
相关论文
共 50 条
  • [1] The Role of the Indole in Important Organocatalytic Enantioselective Friedel-Crafts Alkylation Reactions
    Marques-Lopez, Eugenia
    Diez-Martinez, Alba
    Merino, Pedro
    Herrera, Raquel P.
    CURRENT ORGANIC CHEMISTRY, 2009, 13 (16) : 1585 - 1609
  • [2] Catalytic enantioselective Friedel-Crafts alkylation at the 2-position of indole with simple enones
    Blay, Gonzalo
    Fernandez, Isabel
    Pedro, Jose R.
    Vila, Carlos
    TETRAHEDRON LETTERS, 2007, 48 (38) : 6731 - 6734
  • [3] FRIEDEL-CRAFTS REACTIONS OF 2-SUBSTITUTED OXETANES
    VIRTANEN, PO
    PELTONEN, S
    HYYPPA, J
    SUOMEN KEMISTILEHTI, 1973, 46 (11-1): : 171 - 172
  • [4] Organocatalytic formal [2+2] cycloaddition initiated by vinylogous Friedel-Crafts alkylation: enantioselective synthesis of substituted cyclobutane derivatives
    Duan, Guo-Jian
    Ling, Jun-Bing
    Wang, Wei-Ping
    Luo, Yong-Chun
    Xu, Peng-Fei
    CHEMICAL COMMUNICATIONS, 2013, 49 (41) : 4625 - 4627
  • [5] FRIEDEL-CRAFTS REACTIONS OF 2-SUBSTITUTED OXETANES
    VIRTANEN, PO
    PELTONEN, S
    HYYPPA, J
    ACTA CHEMICA SCANDINAVICA, 1973, 27 (10): : 3944 - 3952
  • [6] 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
  • [7] One-Pot Synthesis of Polynuclear Indole Derivatives by Friedel-Crafts Alkylation of γ-Hydroxybutyrolactams
    Abaev, Vladimir T.
    Aksenov, Nicolai A.
    Aksenov, Dmitrii A.
    Aleksandrova, Elena V.
    Akulova, Alesia S.
    Kurenkov, Igor A.
    Leontiev, Alexander V.
    Aksenov, Alexander V.
    MOLECULES, 2023, 28 (07):
  • [8] Enantioselective Friedel-Crafts alkylation of indole with nitroalkenes in the presence of bifunctional squaramide organocatalysts
    Dundar, Esra
    Tanyeli, Cihangir
    TETRAHEDRON LETTERS, 2021, 73
  • [9] Highly stereoselective imidazolethiones mediated Friedel-Crafts alkylation of indole derivatives
    Liang, Xianrui
    Li, Shuangmin
    Su, Weike
    TETRAHEDRON LETTERS, 2012, 53 (03) : 289 - 291
  • [10] Synthesis of enantiopure (S)-indolylglycine by organocatalyzed Friedel-Crafts alkylation of indole
    Wanner, Martin J.
    Hauwert, Peter
    Schoemaker, Hans E.
    de Gelder, Rene
    van Maarseveen, Jan H.
    Hiemstra, Henk
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (01) : 180 - 185