Highly Enantioselective Friedel-Crafts Alkylation/N-Hemiacetalization Cascade Reaction with Indoles

被引:153
|
作者
Cheng, Hong-Gang [1 ]
Lu, Liang-Qiu [1 ]
Wang, Tao [1 ]
Yang, Qing-Qing [1 ]
Liu, Xiao-Peng [1 ]
Li, Yang [1 ]
Deng, Qiao-Hui [1 ]
Chen, Jia-Rong [1 ]
Xiao, Wen-Jing [1 ,2 ]
机构
[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
基金
美国国家科学基金会;
关键词
alkylation; asymmetric catalysis; chiral Lewis acids; heterocycles; indoles; BETA; GAMMA-UNSATURATED ALPHA-KETOESTERS; ALLYLIC ALKYLATION; PHOSPHORIC-ACID; N-ALLYLATION; CYCLIZATION; CONSTRUCTION; PYRROLOINDOLINES; HYDROARYLATION; CATALYSIS; MICHAEL;
D O I
10.1002/anie.201209998
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new ring for your indole: An unprecedented copper-catalyzed enantioselective Friedel-Crafts alkylation/N-hemiacetalization cascade reaction with indoles and β,γ-unsaturated α-ketoesters is reported. This mild strategy provides new access to various synthetically and biologically important 2,3-dihydro-1H-pyrrolo[1,2-a]indoles in a highly enantioselective manner. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:3250 / 3254
页数:5
相关论文
共 50 条
  • [1] Heteroarylidene-tethered bis(oxazoline) copper complexes catalyzed cascade reaction involving asymmetric Friedel-Crafts alkylation/N-hemiacetalization of indoles with β,γ-unsaturated α-ketoester
    Ma, Hong-Li
    Li, Jia-Qi
    Sun, Lu
    Hou, Xu-He
    Zhang, Zhen-Hua
    Fu, Bin
    TETRAHEDRON, 2015, 71 (22) : 3625 - 3631
  • [2] Enantioselective Construction of Tetrahydro-α-Carbolines via Organocatalytic Friedel-Crafts Alkylation/N-Hemiacetalization of 2-Aminoindoles with Enals
    Liu, Xiaochun
    Ding, Xiang-Feng
    Liu, Yang-Zi
    Deng, Wei-Ping
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [3] Catalytic Asymmetric C-7 Friedel-Crafts Alkylation/N-Hemiacetalization of 4-Aminoindoles
    He, Hualing
    Cao, Yang
    Xu, Jun
    Antilla, Jon C.
    ORGANIC LETTERS, 2021, 23 (08) : 3010 - 3014
  • [4] FRIEDEL-CRAFTS ALKYLATION OF INDOLES
    BUDYLIN, VA
    YERMOLENKO, MS
    KOST, AN
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1978, (07): : 921 - 924
  • [5] 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
  • [6] Organocatalytic Enantioselective Friedel-Crafts Reaction of Phenanthrenequinones and Indoles
    Jin, Yan
    Sun, Yuhong
    Yu, Yue
    Zhao, Jiao
    Zheng, Mingshan
    Wang, Liming
    Jin, Ying
    MOLECULES, 2025, 30 (01):
  • [7] Enantioselective Friedel-Crafts reaction with indoles and ethyl trifluoropyruvate
    Zhang, Peng
    Wolf, Christian
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [8] Highly enantioselective Friedel-Crafts reaction of indoles with imines by a chiral phosphoric acid
    Kang, Qiang
    Zhao, Zhuo-An
    You, Shu-Li
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (06) : 1484 - +
  • [9] Highly regioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated N-acylbenzotriazoles
    Zou, Xuefei
    Wang, Xiaoxia
    Cheng, Cungui
    Kong, Lichun
    Mao, Hui
    TETRAHEDRON LETTERS, 2006, 47 (22) : 3767 - 3771
  • [10] Friedel-Crafts alkylation of indoles with trichloroacetimidates
    Suzuki, Tamie
    Chisholm, John D.
    TETRAHEDRON LETTERS, 2019, 60 (19) : 1325 - 1329