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
  • [21] Catalytic Asymmetric α-Acylation of Tertiary Amines Mediated by a Dual Catalysis Mode: N-Heterocyclic Carbene and Photoredox Catalysis
    DiRocco, Daniel A.
    Rovis, Tomislav
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (19) : 8094 - 8097
  • [22] Primary Amine Functionalized N-Heterocyclic Carbene Complexes of Iridium: Synthesis, Structure, and Catalysis
    O, Wylie W. N.
    Lough, Alan J.
    Morris, Robert H.
    ORGANOMETALLICS, 2013, 32 (14) : 3808 - 3818
  • [23] N-Heterocyclic Carbene Catalyzed Asymmetric Synthesis of Dihydropyranothiazoles via Azolium Enolate Intermediates
    Li, Sun
    Chen, Xiang-Yu
    Sheng, He
    von Essen, Carolina
    Rissanen, Kari
    Enders, Dieter
    SYNTHESIS-STUTTGART, 2018, 50 (05): : 1047 - 1052
  • [24] Synthesis of Thioesters from Aldehydes via N-Heterocyclic Carbene (NHC) Catalyzed Radical Relay
    Man, Yunquan
    Zeng, Xiaojun
    Xu, Bo
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (17)
  • [25] Regio- and enantioselective umpolung gem-difluoroallylation of hydrazones via palladium catalysis enabled by N-heterocyclic carbene ligand
    Huang, Shuai
    Tong, Fei-Fei
    Bai, Da-Chang
    Zhang, Gao-Peng
    Jiang, Yang-Jie
    Zhang, Bo
    Leng, Xuebing
    Guo, Ying-Long
    Wan, Xiao-Long
    Zhang, Xingang
    Ding, Chang-Hua
    Hou, Xue-Long
    NATURE COMMUNICATIONS, 2021, 12 (01)
  • [26] Updating the Benzoin Condensation of Benzaldehyde Using Microwave-Assisted Organic Synthesis and N-Heterocyclic Carbene Catalysis
    Morgan, John P.
    Torres, Elizabeth E.
    Averill, Richard
    Brody, Alex M.
    JOURNAL OF CHEMICAL EDUCATION, 2023, 100 (02) : 986 - 990
  • [27] Fast Enantio- and Chemoselective Arylation of Ketones with Organoboronic Esters Enabled by Nickel/N-Heterocyclic Carbene Catalysis
    Cai, Yuan
    Ruan, Lin-Xin
    Rahman, Abdul
    Shi, Shi-Liang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (10) : 5262 - 5267
  • [28] 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
  • [29] Recent Advances in Organic Synthesis Using Light-Mediated N-Heterocyclic Carbene Catalysis
    Marzo, Leyre
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (33) : 4603 - 4610
  • [30] A Cationic Zinc Hydride Cluster Stabilized by an N-Heterocyclic Carbene: Synthesis, Reactivity, and Hydrosilylation Catalysis
    Rit, Arnab
    Zanardi, Alessandro
    Spaniol, Thomas P.
    Maron, Laurent
    Okuda, Jun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (48) : 13273 - 13277