Catalytic Enantioselective Friedel-Crafts Reactions of Naphthols and Electron-Rich Phenols

被引：48
|
作者：
Montesinos-Magraner, Marc [1 ]
Vila, Carlos [1 ]
Blay, Gonzalo [1 ]
Pedro, Jose R. [1 ]
机构：
[1] Univ Valencia, Fac Quim, Dept Quim Organ, Dr Moliner 50, E-46100 Valencia, Spain
来源：
SYNTHESIS-STUTTGART | 2016年 / 48卷 / 14期
关键词：
Friedel-Crafts reactions; asymmetric catalysis; hydroxyarenes; ketones; imines; nitroalkenes; unsaturated carbonyl compounds; allylation; ASYMMETRIC ALLYLIC DEAROMATIZATION; IN-SITU; ACTIVATED PHENOLS; CASCADE REACTION; ALKYLATION; CONSTRUCTION; 2-NAPHTHOLS; 1-NAPHTHOLS; KETIMINES; ISATINS;
D O I：
10.1055/s-0035-1561434
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The enantioselective Friedel-Crafts reaction is a powerful tool for the construction of benzylic stereocenters in a stereodefined manner. Significant advances have already been achieved with heteroarenes such as indoles and pyrroles; however, the reaction with homoarenes is less developed. This short review covers the most relevant literature on enantioselective Friedel-Crafts reactions with naphthols and phenols. 1 Introduction 2 Friedel-Crafts Reactions Involving 1,2-Nucleophilic Addition to C=X Bonds 3 Friedel-Crafts Reactions Involving Conjugate Nucleophilic Addition to Electrophilic C=C Bonds 4 Friedel-Crafts Reactions Involving -Allylic Complexes as Electrophiles 5 ipso-Friedel-Crafts Reactions 6 Conclusions
引用
收藏
页码：2151 / 2164
页数：14
相关论文
共 50 条
  • [1] Organocatalytic, Enantioselective Friedel-Crafts Reaction of Indoles in the Carbocyclic Ring and Electron-Rich Phenols
    Liu, Jin-Yu
    Yang, Xie-Chao
    Lu, Hong
    Gu, Yu-Cheng
    Xu, Peng-Fei
    ORGANIC LETTERS, 2018, 20 (08) : 2190 - 2194
  • [2] Enantioselective organocatalytic Friedel-Crafts reaction of electron-rich phenols and isatins by Takemoto's thiourea catalyst
    Chen, Zhe
    Wang, Liming
    Tian, Wenqin
    Jin, Ying
    Qin, Xin
    MOLECULAR DIVERSITY, 2024, 28 (03) : 1733 - 1742
  • [3] Continuous flow Friedel-Crafts acetylation of phenols and electron-rich arenes and heteroarenes
    Saint-Jacques, Kevin
    Charette, Andre B.
    JOURNAL OF FLOW CHEMISTRY, 2023, 13 (02) : 193 - 199
  • [4] Organocatalytic Enantioselective aza-Friedel-Crafts Reactions of Pyrazolinone Ketimines with Hydroxyindoles and Electron-Rich Phenols
    Yang, Zhong-Tao
    Yang, Wu-Lin
    Chen, Long
    Sun, Hao
    Deng, Wei-Ping
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (10) : 2049 - 2054
  • [5] Organocatalytic Enantioselective Friedel-Crafts Reaction of Sesamol and Electron-rich Phenols with Alkylideneindolenine Intermediates Generated from Arylsulfonyl Indoles
    Chang, Chia-Hao
    Han, Jeng-Liang
    CHEMISTRYSELECT, 2016, 1 (18): : 5628 - 5632
  • [6] Organocatalytic Enantioselective Friedel-Crafts Reactions of 1-Naphthols with Aldimines
    Liu, Guixia
    Zhang, Shilei
    Li, Hao
    Zhang, Tangzhi
    Wang, Wei
    ORGANIC LETTERS, 2011, 13 (05) : 828 - 831
  • [7] Enantioselective Friedel-Crafts reaction of electron-rich alkenes catalyzed by chiral bronsted acid
    Terada, Masahiro
    Sorimachi, Keiichi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (02) : 292 - 293
  • [8] A Quinine-Squaramide Catalyzed Enantioselective Aza-Friedel-Crafts Reaction of Cyclic Trifluoromethyl Ketimines with Naphthols and Electron-Rich Phenols
    Zhou, Ding
    Huang, Zheng
    Yu, Xueting
    Wang, Youxin
    Li, Jian
    Wang, Wei
    Xie, Hexin
    ORGANIC LETTERS, 2015, 17 (22) : 5554 - 5557
  • [9] Enantioselective Friedel-Crafts Alkylation Reactions of β-Naphthols with Donor-Acceptor Aminocyclopropanes
    Zhu, Man
    Wang, Dong-Chao
    Xie, Ming-Sheng
    Qu, Gui-Rong
    Guo, Hai-Ming
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (58) : 15512 - 15516
  • [10] Friedel-Crafts reaction of electron-rich (het)arenes with nitroalkenes
    Feofanov, Mikhail N.
    Averin, Alexei D.
    Beletskaya, Irina P.
    MENDELEEV COMMUNICATIONS, 2019, 29 (02) : 138 - 139
12345