Recent Advance in Catalytic Asymmetric Friedel-Crafts Reactions

被引:11
作者
Zhang, Yu [1 ]
Liu, Xiaohua [1 ]
Lin, Lili [1 ]
Feng, Xiaoming [1 ]
机构
[1] Sichuan Univ, Coll Chem, Chengdu 610064, Peoples R China
基金
中国国家自然科学基金;
关键词
asymmetric catalysis; Friedel-Crafts reaction; phenols; pyrroles; furans; ENANTIOSELECTIVE SYNTHESIS; HETEROAROMATIC-COMPOUNDS; TETHERED BIS(OXAZOLINE); ACTIVATED PHENOLS; ALKYLATION; PYRROLES; INDOLES; NAPHTHOLS; CONSTRUCTION; FURANS;
D O I
10.7536/PC171121
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalytic asymmetric Friedel-Crafts reaction is one of the most efficient methods for the construction of optically active aryl-or heteroaryl-containing compounds. Since Friedel and Crafts reported the first example in 1877, this reaction has attracted wide attention. In recent twenty years, asymmetric catalytic Friedel-Crafts reaction has been well studied in the presence of a number of chiral bifunctional organocatalysts (such as derivatives of cinchona alkaloids, chiral prolinol ethers, chiral phosphoric acids, chiral thiourea, etc.)and various metal and chiral ligand (chiral N,N'-dioxide, chiral bis (oxazoline), chiral Schiff base) complexes. In this paper, we summarize the recent progress in asymmetric Friedel-Crafts reactions of phenols, pyrroles, furans and thiophenes. Finally, the deficiencies as well as the perspective of the Friedel-Crafts reaction have been highlighted.
引用
收藏
页码:491 / 504
页数:14
相关论文
共 87 条
  • [1] Enantioselective Friedel-Crafts Alkylation of Furans and Indoles with Simple α,β-Unsaturated Ketones Catalyzed by Oxazaborolidinone
    Adachi, Shinya
    Tanaka, Fumi
    Watanabe, Kazuya
    Watada, Atsushi
    Harada, Toshiro
    [J]. SYNTHESIS-STUTTGART, 2010, (15): : 2652 - 2669
  • [2] Oxazaborolidinone-Catalyzed Enantioselective Friedel-Crafts Alkylation of Furans and Indoles with α,β-Unsaturated Ketones
    Adachi, Shinya
    Tanaka, Fumi
    Watanabe, Kazuya
    Harada, Toshiro
    [J]. ORGANIC LETTERS, 2009, 11 (22) : 5206 - 5209
  • [3] Catalytic and highly enantioselective Friedel-Crafts type reactions of heteroaromatic compounds with trifluoropyruvate and glyoxylate by a dicationic palladium complex
    Aikawa, Kohsuke
    Asai, Yuya
    Hioki, Yuta
    Mikami, Koichi
    [J]. TETRAHEDRON-ASYMMETRY, 2014, 25 (15) : 1104 - 1115
  • [4] N,N′-Dioxide Scandium(III)-Catalyzed Asymmetric Aza-Friedel-Crafts Reaction of Sesamol with Aldimines
    Bai, Sha
    Liao, Yuting
    Lin, Lili
    Luo, Weiwei
    Liu, Xiaohua
    Feng, Xiaoming
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (21) : 10662 - 10668
  • [5] Catalytic Asymmetric Friedel-Crafts Reaction of Activated Phenols and 4-Oxo-4-arylbutenoates
    Bai, Sha
    Liu, Xiaohua
    Wang, Zhen
    Cao, Weidi
    Lin, Lili
    Feng, Xiaoming
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (11-12) : 2096 - 2100
  • [6] A journey across recent advances in catalytic and stereoselective alkylation of indoles
    Bandini, M
    Melloni, A
    Tommasi, S
    Umani-Ronchi, A
    [J]. SYNLETT, 2005, (08) : 1199 - 1222
  • [7] Asymmetric Friedel-Crafts Reactions of Indole and its Derivatives
    Beletskaya, Irina P.
    Averin, Alexei D.
    [J]. CURRENT ORGANOCATALYSIS, 2016, 3 (01) : 60 - 83
  • [8] Efficient stereoselective nucleophilic addition of pyrroles to chiral nitrones
    Berini, Christophe
    Minassian, Frederic
    Pelloux-Leon, Nadia
    Denis, Jean-Noel
    Vallee, Yannick
    Philouze, Christian
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (14) : 2574 - 2586
  • [9] Enantioselective Zirconium-Catalyzed Friedel-Crafts Alkylation of Pyrrole with Trifluoromethyl Ketones
    Blay, Gonzalo
    Fernandez, Isabel
    Monleon, Alicia
    Pedro, Jose R.
    Vila, Carlos
    [J]. ORGANIC LETTERS, 2009, 11 (02) : 441 - 444
  • [10] The first enantioselective organocatalytic Mukaiyama- Michael reaction:: A direct method for the synthesis of enantioenriched γ-butenolide architecture
    Brown, SP
    Goodwin, NC
    MacMillan, DWC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) : 1192 - 1194