The N,N′-dioxide/Ni(II)-catalyzed asymmetric inverse-electron-demand hetero-Diels-Alder reaction of methyleneindolinones with hetero-substituted alkenes

被引:0
|
作者
Zhou, Yuhang [1 ]
Lin, Lili [1 ]
Yin, Chengkai [1 ]
Wang, Zhengmeng [1 ]
Liu, Xiaohua [1 ]
Feng, Xiaoming [1 ]
机构
[1] Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China
基金
中国国家自然科学基金;
关键词
BETA; GAMMA-UNSATURATED ALPHA-KETOESTERS; 1,3-DIPOLAR CYCLOADDITION REACTION; HIGHLY ENANTIOSELECTIVE SYNTHESIS; DIHYDROPYRAN-FUSED INDOLES; BINARY-ACID CATALYSIS; OXINDOLES; COMPLEX; CONSTRUCTION; MOIETIES; LIGANDS;
D O I
10.1039/C5CC04245C
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The highly efficient catalytic asymmetric inverse-electron-demand hetero-Diels-Alder reaction of methyleneindolinones with hetero-substituted alkenes has been accomplished under mild reaction conditions. In the presence of chiral N,N'-dioxide/Ni(II) complexes, a wide range of optically active dihydropyran-fused indoles were obtained in up to 99% yield, >95 : 5 dr and 99% ee.
引用
收藏
页码:11689 / 11692
页数:4
相关论文
共 50 条
  • [1] Catalytic Asymmetric Inverse-Electron-Demand Hetero-Diels Alder Reaction of Dioxopyrrolidines with Hetero-Substituted Alkenes
    Hu, Xinyue
    Zhou, Yuhang
    Lu, Yan
    Zou, Sijia
    Lu, Lili
    Liu, Xiaohua
    Feng, Xiaoming
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (15): : 8679 - 8687
  • [2] N,N′-Dioxide/Nickel(II)-Catalyzed Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reaction of β,γ-Unsaturated α-Ketoesters with Enecarbamates
    Zhou, Yuhang
    Zhu, Yin
    Lin, Lili
    Zhang, Yulong
    Zheng, Jianfeng
    Liu, Xiaohua
    Feng, Xiaoming
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (50) : 16753 - 16758
  • [3] Catalytic Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reactions
    Xie, Mingsheng
    Lin, Lili
    Feng, Xiaoming
    [J]. CHEMICAL RECORD, 2017, 17 (12): : 1184 - 1202
  • [4] IronIII-catalyzed asymmetric inverse-electron-demand hetero-Diels-Alder reaction of dioxopyrrolidines with simple olefins
    Zhan, Tangyu
    Zhou, Liang
    Zhou, Yuqiao
    Yang, Bingqian
    Feng, Xiaoming
    Liu, Xiaohua
    [J]. CHEMICAL SCIENCE, 2024, 15 (13) : 4797 - 4803
  • [5] Inverse-electron-demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketophosphonates catalyzed by prolinal dithioacetals
    Samanta, Sampak
    Krause, Jonathan
    Mandal, Tanmay
    Zhao, Cong-Gui
    [J]. ORGANIC LETTERS, 2007, 9 (14) : 2745 - 2748
  • [6] The first organocatalytic enantioselective inverse-electron-demand hetero-Diels-Alder reaction
    Juhl, K
    Jorgensen, KA
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (13) : 1498 - 1501
  • [7] Asymmetric Diels-Alder and Inverse-Electron-Demand Hetero-Diels Alder Reactions of β,γ-Unsaturated α-Ketoesters with Cyclopentadiene Catalyzed by N,N′-Dioxide Copper(II) Complex
    Zhu, Yin
    Chen, Xiaohong
    Xie, Mingsheng
    Dong, Shunxi
    Qiao, Zhen
    Lin, Lili
    Liu, Xiaohua
    Feng, Xiaoming
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (39) : 11963 - 11968
  • [8] Organocatalyzed asymmetric inverse-electron-demand hetero-Diels-Alder reaction of α,β-unsaturated trifluoromethyl ketones and aldehydes
    Zhao, Yan
    Wang, Xiao-Jin
    Liu, Jin-Tao
    [J]. SYNLETT, 2008, (07) : 1017 - 1020
  • [9] Chiral Bisguanidine-Catalyzed Inverse-Electron-Demand Hetero-Diels-Alder Reaction of Chalcones with Azlactones
    Dong, Shunxi
    Liu, Xiaohua
    Chen, Xiaohong
    Mei, Fang
    Zhang, Yulong
    Gao, Bo
    Lin, Lili
    Feng, Xiaoming
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (31) : 10650 - 10651
  • [10] Organocatalytic Strategies for the Development of the Enantioselective Inverse-electron-demand Hetero-Diels-Alder Reaction
    Laina-Martin, Victor
    Fernandez-Salas, Jose A.
    Aleman, Jose
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (49) : 12509 - 12520