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
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 11期
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
  • [31] Monodentate N-Ligand-Directed Bifunctional Transition-Metal Catalysis: Highly Enantioselective Friedel-Crafts Alkylation of Indoles with Nitroalkenes
    Guo, Fengfeng
    Lai, Guoyin
    Xiong, Shunshun
    Wang, Sujing
    Wang, Zhiyong
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (22) : 6438 - 6441
  • [32] Enantioselective Friedel-Crafts Alkylation Reaction of Pyrroles with N-Unprotected Alkynyl Trifluoromethyl Ketimines
    Uchikura, Tatsuhiro
    Aruga, Kureha
    Suzuki, Riku
    Akiyama, Takahiko
    ORGANIC LETTERS, 2022, 24 (25) : 4699 - 4703
  • [33] SYNTHESIS OF KETONIC INDOLES BY FRIEDEL-CRAFTS REACTION
    ROSSEELS, G
    PEIREN, M
    MATTEAZZI, J
    WOUTERS, G
    PROST, M
    BULLETIN DES SOCIETES CHIMIQUES BELGES, 1975, 84 (03): : 263 - 265
  • [34] Organocatalytic Enantioselective Friedel-Crafts Alkylation Reactions of Pyrroles
    Gavina, Daniel
    Escolano, Marcos
    Torres, Javier
    Alzuet-Pina, Gloria
    Sanchez-Rosello, Maria
    del Pozo, Carlos
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (14) : 3439 - 3470
  • [35] Enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by a bis(oxazoline)-Cu(II) complex
    Singh, Pradeep K.
    Bisai, Alakesh
    Singh, Vinod K.
    TETRAHEDRON LETTERS, 2007, 48 (07) : 1127 - 1129
  • [36] Highly enantioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated ketones with simple Cu(II)-oxazoline-imidazoline catalysts
    Barakat, Assem
    Islam, Mohammad Shahidul
    Al Majid, Abdullah M. A.
    Al-Othman, Zeid Abdullah
    TETRAHEDRON, 2013, 69 (25) : 5185 - 5192
  • [37] Enantioselective Friedel-Crafts Alkylation between Nitroalkenes and Indoles Catalyzed by Charge Activated Thiourea Organocatalysts
    Fan, Yang
    Kass, Steven R.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (24): : 13288 - 13296
  • [38] Synthesis of Magnetic Nanoparticles and Polymer Supported Imidazolidinone Catalysts for Enantioselective Friedel-Crafts Alkylation of Indoles
    Pagoti, Sreenivasarao
    Ghosh, Tridev
    Dash, Jyotirmayee
    CHEMISTRYSELECT, 2016, 1 (15): : 4386 - 4391
  • [39] Catalytic Enantioselective Friedel-Crafts Alkylation of Indoles with Fumarate Derivatives in the Presence of Chiral Palladium Complexes
    Lee, Hyun Joo
    Kim, Dae Young
    SYNLETT, 2012, (11) : 1629 - 1632
  • [40] Dianhydrohexitols: new tools for organocatalysis. Application in enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes
    Chen, Ling-Yan
    Guillarme, Stephane
    Saluzzo, Christine
    ARKIVOC, 2013, : 227 - 244
12345