N-Heterocyclic Carbene/Copper Cooperative Catalysis for the Asymmetric Synthesis of Spirooxindoles

被引：177
|
作者：
Zhang, Zi-Jing [1 ,2 ]
Zhang, Ling [1 ,2 ]
Geng, Rui-Long [1 ,2 ]
Song, Jin [1 ,2 ]
Chen, Xiao-Hua [3 ]
Gong, Liu-Zhu [1 ,2 ,4 ]
机构：
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
[4] Chinese Acad Sci, Ctr Excellence Mol Synth, Hefei 230026, Anhui, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 35期
关键词：
cooperative catalysis; copper; enals; N-heterocyclic carbenes; spirooxindoles; ISATIN-DERIVED ENALS; ENANTIOSELECTIVE SYNTHESIS; SYNERGISTIC CATALYSIS; DUAL CATALYSIS; 3+3 ANNULATION; NHC CATALYSIS; ACCESS; ORGANOCATALYSIS; ALLYLATION; SCAFFOLDS;
D O I：
10.1002/anie.201907188
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Highly enantioselective [3+3] and [3+4] annulations of isatin-derived enals with ethynylethylene carbonates and ethynyl benzoxazinanones are enabled by NHC/cooper cooperative catalysis, leading to a big library of spirooxindole derivatives in high structural diversity and enantioselectivity (up to 99 % ee). Both reactions represent a nicely synergistic integration of NHC and copper catalysis, in which both catalysts activate the substrates and the chiral NHC perfectly controls the stereochemistry.
引用
收藏
页码：12190 / 12194
页数：5
相关论文
共 50 条
  • [21] Enantioselective Synthesis of Substituted δ-Lactones by Cooperative Oxidative N-Heterocyclic Carbene and Lewis Acid Catalysis
    Bera, Srikrishna
    Daniliuc, Constantin G.
    Studer, Armido
    ORGANIC LETTERS, 2015, 17 (20) : 4940 - 4943
  • [22] Diastereodivergent synthesis of enantioenriched α,β-disubstituted γ-butyrolactones via cooperative N-heterocyclic carbene and Ir catalysis
    Singha, Santanu
    Serrano, Eloisa
    Mondal, Shobhan
    Daniliuc, Constantin G.
    Glorius, Frank
    NATURE CATALYSIS, 2020, 3 (01) : 48 - 54
  • [23] Diastereodivergent synthesis of enantioenriched α,β-disubstituted γ-butyrolactones via cooperative N-heterocyclic carbene and Ir catalysis
    Santanu Singha
    Eloisa Serrano
    Shobhan Mondal
    Constantin G. Daniliuc
    Frank Glorius
    Nature Catalysis, 2020, 3 : 48 - 54
  • [24] Enantioselective Synthesis of δ-Carbolinones via N-Heterocyclic Carbene Catalysis
    Zhang, Simiao
    Lin, Chen
    Liu, Chaolei
    Du, Ding
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (15): : 10441 - 10448
  • [25] N-Heterocyclic carbene/palladium synergistic catalysis in organic synthesis
    Debnath, Chhanda
    Bhoi, Saswat Ranjan
    Gandhi, Shikha
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (23) : 4613 - 4624
  • [26] Advances in N-Heterocyclic Carbene Catalysis for Natural Product Synthesis
    Que, Yonglei
    He, Haibing
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (37) : 5917 - 5925
  • [27] Synthesis of unsymmetrical benzils using N-heterocyclic carbene catalysis
    Suzuki, Yumiko
    Md, Abu Bakar
    Tanoi, Takashi
    Nomura, Naoko
    Sato, Masayuki
    TETRAHEDRON, 2011, 67 (25) : 4710 - 4715
  • [28] N-heterocyclic carbene-copper(I) complexes in homogeneous catalysis
    Diez-Gonzalez, Silvia
    Nolan, Steven P.
    SYNLETT, 2007, (14) : 2158 - 2167
  • [29] N-Heterocyclic Carbene-Catalyzed Asymmetric Synthesis of Cyclopentenones
    Chen, Zhizhou
    Kong, Xiangwen
    Niu, Shengtong
    Yang, Shuang
    Liu, Jinggong
    Chen, Bolai
    Luo, Benlong
    Zhou, Changyu
    Ding, Chenglin
    Fang, Xinqiang
    ORGANIC LETTERS, 2021, 23 (09) : 3403 - 3408
  • [30] Switching Reaction Pathways by Cooperative Catalysis of N-Heterocyclic Carbene and Lewis Acids
    Wang Leming
    Wang Qian
    Chen Jiean
    Huang Yong
    ACTA CHIMICA SINICA, 2018, 76 (11) : 850 - 856
12345