Relay Organophotoredox/N-Heterocyclic Carbene Catalysis-Enabled Asymmetric Synthesis of Dibenzoxazepine-Fused Pyrrolidinones

被引:6
作者
Hussain, Yaseen [1 ]
Sharma, Deepak [1 ]
Tamanna [1 ]
Chauhan, Pankaj [1 ]
机构
[1] Indian Inst Technol Jammu, Dept Chem, Jagti 181221, Jammu & Kashmir, India
关键词
PHOTOREDOX CATALYSIS; COOPERATIVE PHOTOREDOX; TERTIARY-AMINES; DUAL CATALYSIS; ALDEHYDES; UMPOLUNG; KETONES; ACID;
D O I
10.1021/acs.orglett.3c00685
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An unprecedented highly stereoselective synthesis of pyrrolo[1,2-d][1,4]oxazepin-3(2H)-ones has been accomplished via photoredox/N-heterocyclic carbene (NHC) relay catalysis. A wide range of substituted dibenzoxazepines and aryl/hetereoaryl enals were well accommodated under the organic photoredox catalysis- promoted amine oxidation to generate the imines, followed by a NHC-catalyzed [3 + 2] annulation reaction to achieve excellent diastereo- and enantioselectivities of the dibenzoxazepine-fused pyrrolidinones.
引用
收藏
页码:2520 / 2524
页数:5
相关论文
共 50 条
  • [1] Recent Advances in the Synthesis of Cyanides Enabled by N-Heterocyclic Carbene Catalysis
    Cai Yuanlin
    Lu Ya
    Nie Guihua
    Jin Zhichao
    Chi Yonggui
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (09) : 3135 - 3145
  • [2] N-Heterocyclic Carbene/Copper Cooperative Catalysis for the Asymmetric Synthesis of Spirooxindoles
    Zhang, Zi-Jing
    Zhang, Ling
    Geng, Rui-Long
    Song, Jin
    Chen, Xiao-Hua
    Gong, Liu-Zhu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (35) : 12190 - 12194
  • [3] Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update
    Yang Shuang
    Fang Xinqiang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (02) : 448 - 480
  • [4] Oxidative Asymmetric [2+3] Annulation of Aldehydes with Azomethine Imines Enabled by N-Heterocyclic Carbene Catalysis
    Yuan, Shim
    Luo, Yuchen
    Peng, Jingyi
    Miao, Maozhong
    Xu, Jianfeng
    Ren, Hongjun
    ORGANIC LETTERS, 2017, 19 (22) : 6100 - 6103
  • [5] Versatile Relay and Cooperative Palladium(0) N-Heterocyclic Carbene/Copper(I) N-Heterocyclic Carbene Catalysis for the Synthesis of Tri- and Tetrasubstituted Alkenes
    Lesieur, Mathieu
    Bidal, Yannick D.
    Lazreg, Faima
    Nahra, Fady
    Cazin, Catherine S. J.
    CHEMCATCHEM, 2015, 7 (14) : 2108 - 2112
  • [6] Radical Relay Trichloromethylacylation of Alkenes through N-Heterocyclic Carbene Catalysis
    Kusakabe, Mayu
    Nagao, Kazunori
    Ohmiya, Hirohisa
    ORGANIC LETTERS, 2021, 23 (18) : 7242 - 7247
  • [7] Advances in N-Heterocyclic Carbene Catalysis for Natural Product Synthesis
    Que, Yonglei
    He, Haibing
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (37) : 5917 - 5925
  • [8] 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
  • [9] Enantioselective Alkylation of Aldehydes with Organoborons Enabled by Nickel/N-Heterocyclic Carbene Catalysis
    Liu, Song-Yang
    Wang, Zi-Chao
    Shi, Shi-Liang
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (18) : 2161 - 2165
  • [10] Oxidative Enantioselective α-Fluorination of Aliphatic Aldehydes Enabled by N-Heterocyclic Carbene Catalysis
    Li, Fangyi
    Wu, Zijun
    Wang, Jian
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (02) : 656 - 659