Organocatalyzed Asymmetric Friedel-Crafts Reactions: An Update

被引:27
|
作者
Heravi, Majid M. [1 ]
Zadsirjan, Vahideh [1 ]
Heydari, Masumeh [1 ]
Masoumi, Baharak [1 ]
机构
[1] Alzahra Univ, Sch Sci, Dept Chem, POB 1993891176, Tehran, Iran
来源
CHEMICAL RECORD | 2019年 / 19卷 / 11期
关键词
Friedel-Crafts reaction; Organocatalysts; Organocatalysis; Asymmetric Friedel-Crafts reaction; Chiral phosphoric acids; Thioureas; Cinchona alkaloids; Imidazolidinones; Diarylprolinol ethers; CHIRAL BRONSTED ACID; HIGHLY ENANTIOSELECTIVE SYNTHESIS; N-TRIFLYL PHOSPHORAMIDE; ELECTRON-DEFICIENT ALKENES; DIELS-ALDER REACTIONS; SILYL ENOL ETHERS; MICHAEL ADDITION; CONJUGATE ADDITION; ALKYLATION REACTION; NATURAL-PRODUCTS;
D O I
10.1002/tcr.201800190
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Friedel-Crafts alkylation (F-CA) reaction is a special kind of carbon-carbon bond formations, which is frequently being used for the formation of such bond in some aromatic rings in organic synthesis. Its asymmetric variant gives enantiorich products. Commonly, an in situ organocatalyzed asymmetric Friedel-Crafts alkylation (AF-CA) proceeds via generation of an enamine as an intermediate. The organocatalyzed-AF-CA was discovered and established in the mid-1980s and reviewed comprehensively in 2010. In this report, we are trying to update the applications of novel organocatalysts in the AF-CA as a versatile synthetic strategy, which is frequently used in the effective asymmetric synthesis of complex molecules, pharmaceutically important compounds and most importantly in the total synthesis of biologically active natural products.
引用
收藏
页码:2236 / 2340
页数:105
相关论文
共 50 条
  • [1] Organocatalyzed Asymmetric Friedel-Crafts Reactions
    Terrasson, Vincent
    de Figueiredo, Renata Marcia
    Campagne, Jean Marc
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (14) : 2635 - 2655
  • [2] Asymmetric Organocatalyzed Friedel-Crafts Reaction of Trihaloacetaldehydes and Phenols
    Svestka, David
    Otevrel, Jan
    Bobal, Pavel
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (13) : 2174 - 2183
  • [3] Organocatalytic asymmetric Friedel-Crafts reactions
    Sheng, Yi-Fei
    Zhang, An-Jiang
    Zheng, Xiao-Jian
    You, Shu-Li
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (04) : 605 - 616
  • [4] Organocatalyzed Asymmetric Friedel-Crafts Alkylation in the Carbocyclic Ring of Indole
    Mu Hongwen
    Wu Hao
    Gao Yingying
    Jin Ying
    Wang Liming
    [J]. CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2022, 43 (02):
  • [5] Bisphosphorylimides as organocatalysts for asymmetric Friedel-Crafts reactions
    Iafe, Robert
    Ahlberg, Lina
    Thompson, Cristofer
    Diaz, Gloria
    Klasic, Brittney
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [6] Bisphosphorylimides as organocatalysts for asymmetric Friedel-Crafts reactions
    Iafe, Robert
    Ahlberg, Lina
    Dean, Melisa
    Diaz, Gloria
    Klasic, Brittney
    Maynard, Jessica
    Abrous, Leila
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [7] Organocatalyzed Friedel-Crafts arylation of benzylic alcohols
    McCubbin, J. Adam
    Krokhin, Oleg V.
    [J]. TETRAHEDRON LETTERS, 2010, 51 (18) : 2447 - 2449
  • [8] FRIEDEL-CRAFTS REACTIONS
    GROGGINS, PH
    DETWILER, SB
    [J]. INDUSTRIAL AND ENGINEERING CHEMISTRY, 1951, 43 (09): : 1970 - 1974
  • [9] FRIEDEL-CRAFTS REACTIONS
    GROGGINS, PH
    [J]. INDUSTRIAL AND ENGINEERING CHEMISTRY, 1948, 40 (09): : 1608 - 1610
  • [10] FRIEDEL-CRAFTS REACTIONS
    GROGGINS, PH
    DETWILER, SB
    [J]. INDUSTRIAL AND ENGINEERING CHEMISTRY, 1952, 44 (09): : 2012 - 2015