Copper-catalyzed (4+3)-cycloaddition of 4-indolylcarbinols with aziridines: stereoselective synthesis of azepinoindoles

被引：0
|
作者：
Kar, Subhradeep [1 ]
Maharana, Prabhat Kumar [1 ]
Maity, Swagata [1 ]
Trivedi, Vishal [2 ]
Punniyamurthy, Tharmalingam [1 ]
机构：
[1] Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati,781039, India
[2] Department of Biosciences and Bioengineering, Indian Institute of Technology Guwahati, Guwahati,781039, India
来源：
Chemical Communications | 2024年 / 60卷 / 83期
关键词：
Cycloaddition;
D O I：
10.1039/d4cc03544e
中图分类号：
学科分类号：
摘要：
Copper(i)-catalyzed (4+3)-cycloaddition of 4-indolylcarbinols with aziridines has been accomplished to furnish azepinoindoles. The chirality transfer, substrate scope, functional group tolerance, natural product modification and tandem C-C/C-N bond formation are the important practical features. © 2024 The Royal Society of Chemistry.
引用
收藏
页码：12008 / 12011
相关论文
共 50 条
  • [1] Tandem (4+3)-Annulation of Aziridines: Stereoselective Access to Fused Azepinoindoles
    Kar, Subhradeep
    Maharana, Prabhat K.
    Punniyamurthy, Tharmalingam
    Trivedi, Vishal
    [J]. ORGANIC LETTERS, 2023, 25 (49) : 8850 - 8855
  • [2] Stereoselective synthesis of (±)-urechitol A employing [4+3] cycloaddition
    Sumiya, Tatsunobu
    Ishigami, Ken
    Watanabe, Hidenori
    [J]. TETRAHEDRON, 2016, 72 (44) : 6982 - 6987
  • [3] Asymmetric synthesis of tropanes by rhodium-catalyzed [4+3] cycloaddition
    Reddy, Ravisekhara P.
    Davies, Hum M. L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (34) : 10312 - +
  • [4] Gold catalyzed transannular [4+3] cycloaddition reactions
    Craft, Derek T.
    Bailey, Lauren
    Gung, Benjamin W.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [5] A 4+3 cycloaddition approach to the synthesis of (±)-sterpurene
    Harmata, M
    Bohnert, GJ
    [J]. ORGANIC LETTERS, 2003, 5 (01) : 59 - 61
  • [6] Copper-Catalyzed Enantioselective [4π+2σ] Cycloaddition of Bicyclobutanes with Nitrones
    Zhang, Xuan-Ge
    Zhou, Zi-Yang
    Li, Jia-Xin
    Chen, Jun-Jia
    Zhou, Qi-Lin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, : 27274 - 27281
  • [7] Gold-catalyzed transannular [4+3] cycloaddition reactions
    Gung, Benjamin W.
    Craft, Derek T.
    [J]. TETRAHEDRON LETTERS, 2009, 50 (22) : 2685 - 2687
  • [8] RhII/ZnII Catalyzed Asymmetric [4+3] Cycloaddition Reaction
    Song, Jin
    Gong, Liuzhu
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (01) : 245 - 246
  • [9] A gold-catalyzed [4+3]-cycloaddition of functionalized dioxines
    Harmata, Michael
    Huang, Chaofeng
    [J]. TETRAHEDRON LETTERS, 2009, 50 (41) : 5701 - 5703
  • [10] Gold-Catalyzed Transannular [4+3] Cycloaddition Reactions
    Gung, Benjamin W.
    Craft, Derek T.
    Bailey, Lauren N.
    Kirschbaum, Kristin
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (02) : 639 - 644
12345