Organocatalytic cascade 1,6-conjugate addition/annulation/tautomerization of functionalized para-quinone methides: Access to chiral 2-amino-4-aryl-4H-chromenes

被引:2
|
作者
Cong Duan [1 ]
Ling Ye [2 ]
Wenqin Xu [1 ]
Xinying Li [1 ]
Feng Chen [1 ]
Zhigang Zhao [1 ]
Xuefeng Li [1 ]
机构
[1] College of Chemistry and Environment Protection Engineering, Southwest Minzu University
[2] Faculty of Geosciences and Environmental Engineering, Southwest Jiaotong University
基金
中国国家自然科学基金; 中央高校基本科研业务费专项资金资助;
关键词
para-Quinone methides; 2-Amino-4-aryl-4H-chromene; Domino reaction; 1,6-Conjugated addition; Enantioselective;
D O I
暂无
中图分类号
O625.6 [芳香族含氮化合物];
学科分类号
摘要
A novel organocatalytic cascade process initiated by 1,6-conjugated addition has been successfully developed. A range of pharmaceutically active 2-amino-4-aryl-4H-chromenes were readily obtained in high yields(88%-99%) and excellent enantiopurities(86%-99% ee). The functionalized para-Quinone methides(p-OMs) could be facilely obtained.
引用
收藏
页码:1273 / 1276
页数:4
相关论文
共 50 条
  • [21] Bis(amino)cyclopropenylidene-Catalyzed 1,6-Conjugate Addition of Aromatic Aldehydes to para-Quinone Methides: Expedient Access to α,α′-Diarylated Ketones
    Ramanjaneyulu, Bandaru T.
    Mahesh, Sriram
    Anand, Ramasamy Vijaya
    ORGANIC LETTERS, 2015, 17 (16) : 3952 - 3955
  • [22] Asymmetric Catalytic 1,6-Conjugate Addition/Aromatization of para-Quinone Methides: Enantioselective Introduction of Functionalized Diarylmethine Stereogenic Centers
    Chu, Wen-Dao
    Zhang, Le-Fen
    Bao, Xu
    Zhao, Xian-He
    Zeng, Chao
    Du, Ji-Yuan
    Zhang, Guo-Biao
    Wang, Fang-Xin
    Ma, Xiao-Yan
    Fan, Chun-An
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) : 9229 - 9233
  • [23] Catalyst-Free 1,6-Conjugate Addition/Aromatization/Sulfonylation of para-Quinone Methides: Facile Access to Diarylmethyl Sulfones
    Liu, Teng
    Liu, Jianjun
    Xia, Shubiao
    Meng, Jie
    Shen, Xianfu
    Zhu, Xiufang
    Chen, Wenchang
    Sun, Chengke
    Cheng, Feixiang
    ACS OMEGA, 2018, 3 (02): : 1409 - 1415
  • [24] Isothiourea-Catalyzed Enantioselective α-Alkylation of Esters via 1,6-Conjugate Addition to para-Quinone Methides
    Arokianathar, Jude N.
    Hartley, Will C.
    McLaughlin, Calum
    Greenhalgh, Mark D.
    Stead, Darren
    Ng, Sean
    Slawin, Alexandra M. Z.
    Smith, Andrew D.
    MOLECULES, 2021, 26 (21):
  • [25] Copper-catalyzed asymmetric 1,6-conjugate addition of in situ generated para-quinone methides with β-ketoesters
    Wang, Yi-Feng
    Wang, Chao-Jie
    Feng, Qing-Zhou
    Zhai, Jing-Jing
    Qi, Suo-Suo
    Zhong, Ai-Guo
    Chu, Ming-Ming
    Xu, Dan-Qian
    CHEMICAL COMMUNICATIONS, 2022, 58 (46) : 6653 - 6656
  • [26] Base-mediated 1,6-conjugate addition of the Seyferth-Gilbert reagent to para-quinone methides
    Gupta, Ashis Kumar
    Ahamad, Shakir
    Vaishanv, Narendra Kumar
    Kant, Ruchir
    Mohanan, Kishor
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (25) : 4623 - 4627
  • [27] Asymmetric Organocatalytic Synthesis of 3-Diarylmethine-Substituted Oxindoles Bearing a Quaternary Stereocenter via 1,6-Conjugate Addition to para-Quinone Methides
    Zhao, Kun
    Zhi, Ying
    Wang, Ai
    Enders, Dieter
    ACS CATALYSIS, 2016, 6 (02): : 657 - 660
  • [28] Catalytic Asymmetric 1,6-Conjugate Addition of para-Quinone Methides: Formation of All-Carbon Quaternary Stereocenters
    Wang, Zhaobin
    Wong, Yuk Fai
    Sun, Jianwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (46) : 13711 - 13714
  • [29] Enantioselective Rauhut-Currier-Type 1,6-Conjugate Addition of Methyl Vinyl Ketone to para-Quinone Methides
    Kang, Tian-Chen
    Wu, Lu-Ping
    Yu, Qi-Wen
    Wu, Xin-Yan
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (27) : 6509 - 6513
  • [30] Metal-Free Regioselective 1,6-Conjugate Addition of Sulfide to para-Quinone Methides: Simple Access to E-Selective Thiaoxacyclophanes
    Kotha, Sambasivarao
    Gupta, Naveen K.
    Solanke, Balaji U.
    CHEMISTRYSELECT, 2023, 8 (34):