Phosphine-catalyzed [3+2] annulation of β-sulfonamido-substituted enones with trans-α-cyano-α,β-unsaturated ketones for the synthesis of highly substituted pyrrolidines

被引:4
|
作者
Gao, Zhenzhen [1 ]
Xie, Lei [1 ]
Ji, Lusha [1 ]
Ma, Xin [1 ]
Li, Xiaojing [1 ]
Liu, Honglei [2 ]
Guo, Hongchao [3 ]
机构
[1] Liaocheng Univ, Sch Pharm, Liaocheng 252000, Shandong, Peoples R China
[2] Qingdao Univ, Coll Mat Sci & Engn, Qingdao 266071, Shandong, Peoples R China
[3] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China
关键词
ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; BAYLIS-HILLMAN CARBONATES; FACILE SYNTHESIS; IMINES; CYCLOADDITION; 3-PYRROLINES; ALLENES;
D O I
10.1039/d1ra07881j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
To synthesize highly substituted pyrrolidines, we developed a phosphine-catalyzed [3 + 2] annulation of beta-sulfonamido-substituted enones with trans-alpha-cyano-alpha,beta-unsaturated ketones. We prepared a series of pyrrolidines under mild conditions with high yields and moderate-to-good diastereoselectivities. A catalytic mechanism for this reaction is suggested.
引用
收藏
页码:40136 / 40139
页数:4
相关论文
共 50 条
  • [1] Phosphine-Catalyzed (4+2) Annulation of δ-Sulfonamido-Substituted Enones with 1,1-Dicyanoalkenes: Synthesis of Piperidine Derivatives
    Liu, Min
    Zhou, Leijie
    Shi, Wangyu
    Hu, Yimin
    Liao, Jianning
    Duan, Zeqing
    Wang, Wei
    Wu, Yongjun
    Zheng, Bing
    Guo, Hongchao
    [J]. ORGANIC LETTERS, 2021, 23 (20) : 7703 - 7707
  • [2] Phosphine-catalyzed [5+1] annulation of δ-sulfonamido-substituted enones with N-sulfonylimines: a facile synthesis of tetrahydropyridines
    Zhou, Leijie
    Yuan, Chunhao
    Zeng, Yuan
    Liu, Honglei
    Wang, Chang
    Gao, Xing
    Wang, Qijun
    Zhang, Cheng
    Guo, Hongchao
    [J]. CHEMICAL SCIENCE, 2018, 9 (07) : 1831 - 1835
  • [3] Phosphine-catalyzed enantioselective [3+2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones
    Zhou, Wei
    Wang, Huamin
    Tao, Mengna
    Zhu, Chao-Ze
    Lin, Tao-Yan
    Zhang, Junliang
    [J]. CHEMICAL SCIENCE, 2017, 8 (06) : 4660 - 4665
  • [4] Phosphine-Catalyzed [3+2] Annulation of β-Sulfonannido-Substituted Enones with Sulfamate-Derived Cyclic Imines
    Shi, Wangyu
    Zhou, Leijie
    Mao, Biming
    Wang, Qijun
    Wang, Chang
    Zhang, Cheng
    Li, Xuefeng
    Xiao, Yumei
    Guo, Hongchao
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (02): : 679 - 686
  • [5] Phosphine-Catalyzed Enantioselective (3+2) Annulation of Vinylcyclopropanes with Imines for the Synthesis of Chiral Pyrrolidines
    Zhang, Fuhao
    Dai, Xuan
    Dai, Lei
    Zheng, Wenrui
    Chan, Wai-Lun
    Tang, Xiaodong
    Zhang, Xumu
    Lu, Yixin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (24)
  • [6] Phosphine-Catalyzed (3+2) Annulation of δ-Acetoxy Allenoates with 2-Sulfonamidomalonate: Synthesis of Highly Substituted 3-Pyrrolines and Mechanistic Insight
    Wang, Dong
    Liu, Wei
    Hong, Yang
    Tong, Xiaofeng
    [J]. ORGANIC LETTERS, 2018, 20 (16) : 5002 - 5005
  • [7] An unexpected phosphine-catalyzed [3+2] annulation. Synthesis of highly functionalized cyclopentenes
    Lu, Zheng
    Zheng, Suqing
    Zhang, Xumu
    Lu, Xiyan
    [J]. ORGANIC LETTERS, 2008, 10 (15) : 3267 - 3270
  • [8] Phosphine-catalyzed [3+2] annulation of α-substituted allenoates with ester-activated α,β-unsaturated imines: a novel variation of the Lu [3+2] cycloaddition reaction
    Tian, Junjun
    He, Zhengjie
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (20) : 2058 - 2060
  • [9] Highly Substituted Cyclohexenes via Phosphine-Catalyzed [4+2] Annulation of Electron-deficient Dienes and Vinyl Ketones
    Chen, Peng
    Zhang, Junyou
    Zhang, Junliang
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (04) : 682 - 685
  • [10] Enantioselective [3+2] annulation of α-substituted allenoates with β,γ-unsaturated N-sulfonylimines catalyzed by a bifunctional dipeptide phosphine
    Ni, Huanzhen
    Yao, Weijun
    Lu, Yixin
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 343 - 348