Organocatalyzed Asymmetric Friedel-Crafts Reactions: An Update

被引:31
|
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
  • [41] Organocatalytic asymmetric Friedel-Crafts alkylation/cascade reactions of naphthols and nitroolefins
    Liu, Tian-Yu
    Cui, Hai-Lei
    Chai, Qian
    Long, Jun
    Li, Bang-Jing
    Wu, Yong
    Ding, Li-Sheng
    Chen, Ying-Chun
    CHEMICAL COMMUNICATIONS, 2007, (22) : 2228 - 2230
  • [42] Studies on aluminium mediated asymmetric Friedel-Crafts hydroxyalkylation reactions of pyridinecarbaldehydes
    Gothelf, AS
    Hansen, T
    Jorgensen, KA
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (08): : 854 - 860
  • [43] FRIEDEL-CRAFTS REACTIONS WITH ORGANIC DIHALIDES
    SISIDO, K
    NOZAKI, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (04) : 961 - 964
  • [44] FRIEDEL-CRAFTS REACTIONS OF ETHYL CYCLOPROPANECARBOXYLATE
    PINNICK, HW
    BROWN, SP
    MCLEAN, EA
    ZOLLER, LW
    JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (18): : 3758 - 3760
  • [45] FRIEDEL-CRAFTS AND RELATED REACTIONS - MISCELLANEOUS REACTIONS
    ZOLLINGE.H
    CHIMIA, 1966, 20 (02) : 71 - &
  • [46] FRIEDEL-CRAFTS REACTIONS OF SILICON HALIDES
    KANNER, B
    PEPE, EJ
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1969, 17 (03) : 490 - &
  • [47] MECHANISTIC ASPECTS OF FRIEDEL-CRAFTS REACTIONS
    NAKANE, R
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1978, 36 (06) : 440 - 453
  • [48] FRIEDEL-CRAFTS REACTIONS WITH INTERCALATED CATALYSTS
    LALANCETTE, JM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1977, 173 (MAR20): : 185 - 185
  • [49] Anomalous Friedel-Crafts reactions with furans
    Gilman, H
    McCorkle, M
    Calloway, NO
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1934, 56 : 745 - 745
  • [50] FRIEDEL-CRAFTS REACTIONS OF SOME ACYLALS
    HURD, CD
    IWASHIGE, T
    JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (09): : 1321 - 1324