CHIRAL PHOSPHORIC ACID CATALYZED ASYMMETRIC FRIEDEL-CRAFTS ALKYLATION OF INDOLES WITH NITROOLEFINS

被引:9
|
作者
Tang, Hong-Ying [1 ]
Zhang, Zhong-Biao [1 ]
机构
[1] Tianjin Normal Univ, Tianjin Key Lab Water Environm & Resources, Tianjin 300387, Peoples R China
关键词
Asymmetric Friedel-Crafts alkylations; enantioselectivities; chiral phosphoric acid; indoles; nitroolefins; TETRAHYDRO-BETA-CARBOLINES; BOND-FORMING REACTIONS; BRONSTED ACID; ENANTIOSELECTIVE ADDITION; NITROALKENES; COMPLEXES; IMINES; ORGANOCATALYSTS; BIS(OXAZOLINE); DISCOVERY;
D O I
10.1080/10426507.2010.536189
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Asymmetric Michael-type Friedel-Crafts (F-C) alkylations of indoles with nitroolefins catalyzed by a chiral H-8-BINOL-based phosphoric acid were investigated. The reactions took place very smoothly in the presence of only 5 mol-% of catalyst at room temperature to afford the desired F-C alkylation products in good yields and with moderate enantioselectivities.
引用
收藏
页码:2038 / 2046
页数:9
相关论文
共 50 条
  • [31] Chiral Bronsted Acid Directed Iron-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with β-Aryl α′-Hydroxy Enones
    Yang, Lei
    Zhu, Qiming
    Guo, Shengmei
    Qian, Bo
    Xia, Chungu
    Huang, Hanmin
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (05) : 1638 - 1645
  • [32] Bronsted Acid-Catalyzed Asymmetric Friedel-Crafts Alkylation of Indoles with Benzothiazole-Bearing Trifluoromethyl Ketone Hydrates
    Wang, Wei
    Xiong, Wenhui
    Wang, Jinping
    Wang, Qiu-An
    Yang, Wen
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (06): : 4398 - 4407
  • [33] Asymmetric Synthesis of β2-Tryptophan Analogues via Friedel-Crafts Alkylation of Indoles with a Chiral Nitroacrylate
    Pavlov, Nikola
    Gilles, Pierre
    Didierjean, Claude
    Wenger, Emmanuel
    Naydenova, Emilia
    Martinez, Jean
    Calmes, Monique
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (15): : 6116 - 6124
  • [34] Enantioselective Friedel-Crafts Alkylation Reaction of Indoles with α-Trifluoromethylated β-Nitrostyrenes Catalyzed by Chiral BINOL Metal Phosphate
    Ibanez, Ignacio
    Kaneko, Mio
    Kamei, Yuto
    Tsutsumi, Ryosuke
    Yamanaka, Masahiro
    Akiyama, Takahiko
    ACS CATALYSIS, 2019, 9 (08) : 6903 - 6909
  • [35] Ni(<sc>ii</sc>)/spiroBox-catalyzed asymmetric Friedel-Crafts alkylation of indoles with nitroalkenes
    Li, Yanshun
    Sun, Shiqin
    Jiao, Luzhen
    Gao, Nanxing
    Cao, Guorui
    RSC ADVANCES, 2025, 15 (10) : 7644 - 7648
  • [36] The mechanism investigation of chiral phosphoric acid-catalyzed Friedel-Crafts reactions - How the chiral phosphoric acid regains the proton
    Liu, Chunhui
    Han, Peilin
    Wu, Xiaoman
    Tang, Mingsheng
    COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2014, 1050 : 39 - 45
  • [37] An Efficient Enantioselective Method for Asymmetric Friedel-Crafts Alkylation of Indoles with α,β-Unsaturated Aldehydes
    Hong, Liang
    Wang, Lei
    Chen, Chao
    Zhang, Bangzhi
    Wang, Rui
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (05) : 772 - 778
  • [38] Chiral phosphoric acid-catalyzed enantioselective Aza-Friedel-Crafts reaction of Indoles
    Terada, Masahiro
    Yokoyama, Shigeko
    Sorimachi, Keiichi
    Uraguchi, Daisuke
    ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (11-12) : 1863 - 1867
  • [39] Highly efficient asymmetric organocatalytic Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes
    Jin, Shangbin
    Li, Chenguang
    Ma, Yuanhui
    Kan, Yuhe
    Zhang, Yong Jian
    Zhang, Wanbin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (17) : 4011 - 4015
  • [40] Asymmetric Synthesis of β-Indolyl Cyclopentanones and Cyclopentylamides with an All-Carbon Quaternary Stereocenter via Chiral Phosphoric Acid Catalyzed Friedel-Crafts Alkylation Reactions
    Liu, Wei
    Rajkumar, Subramani
    Wu, Weihu
    Huang, Ziyu
    Yang, Xiaoyu
    ORGANIC LETTERS, 2019, 21 (10) : 3563 - 3567