Forming All-Carbon Quaternary Centers by Geminal Difunctionalization of Diazo Compounds with N,N-Disubstituted Anilines and Carbonates

被引:6
作者
Chen, Qiang [1 ]
Huang, Tingzhong [1 ]
Shao, Ying [1 ]
Tang, Shengbiao [1 ]
Sun, Jiangtao [1 ]
机构
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China
关键词
TERTIARY AMINE CATALYSIS; 3-COMPONENT REACTIONS; FUNCTIONALIZATION; SEQUENCE; YLIDES; BOND;
D O I
10.1021/acs.joc.2c02730
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel three-component reaction of N,N-disubstituted anilines, diazo compounds, and allylic carbonates has been developed by using a rhodium-palladium dual catalysis, providing an effective protocol for the construction of tetrasubstituted esters bearing an all-carbon quaternary center as well as an allylic moiety in one pot.
引用
收藏
页码:3308 / 3312
页数:5
相关论文
共 34 条
  • [1] Sequential Au(I)/chiral tertiary amine catalysis: a tandem C-H functionalization of anisoles or a thiophene/asymmetric Michael addition sequence to quaternary oxindoles
    Cao, Zhong-Yan
    Zhao, Yu-Lei
    Zhou, Jian
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (12) : 2537 - 2540
  • [2] Enantioselective three-component aminomethylation of α-diazo ketones with alcohols and 1,3,5-triazines
    Che, Jiuwei
    Niu, Li
    Jia, Shikun
    Xing, Dong
    Hu, Wenhao
    [J]. NATURE COMMUNICATIONS, 2020, 11 (01)
  • [3] C-H Functionalization/Asymmetric Michael Addition Cascade Enabled by Relay Catalysis: Metal Carbenoid Used for C-C Bond Formation
    Chen, Dian-Feng
    Zhao, Feng
    Hu, Yue
    Gong, Liu-Zhu
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (40) : 10763 - 10767
  • [4] Au-Catalyzed Formal Allylation of Diazo(thio)oxindoles: Application to Tandem Asymmetric Synthesis of Quaternary Stereocenters
    Cui, Xiao-Yuan
    Zhao, Yu-Lei
    Chen, Yan-Mei
    Dong, Su-Zhen
    Zhou, Feng
    Wu, Hai-Hong
    Zhou, Jian
    [J]. ORGANIC LETTERS, 2021, 23 (12) : 4864 - 4869
  • [5] Modern Organic Synthesis with α-Diazocarbonyl Compounds
    Ford, Alan
    Miel, Hugues
    Ring, Aoife
    Slattery, Catherine N.
    Maguire, Anita R.
    McKervey, M. Anthony
    [J]. CHEMICAL REVIEWS, 2015, 115 (18) : 9981 - 10080
  • [6] Efficient Synthesis of Diaryl Quaternary Centers by Rh(II)/Xantphos Catalyzed Relay C-H Functionalization and Allylic Alkylation
    Ge, Zhaoliang
    Lu, Bin
    Teng, Huailong
    Wang, Xiaoming
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (03)
  • [7] Novel Multicomponent Reactions via Trapping of Protic Onium Ylides with Electrophiles
    Guo, Xin
    Hu, Wenhao
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2013, 46 (11) : 2427 - 2440
  • [8] Catalytic Asymmetric Functionalization of Aromatic C-H Bonds by Electrophilic Trapping of Metal-Carbene-Induced Zwitterionic Intermediates
    Jia, Shikun
    Xing, Dong
    Zhang, Dan
    Hu, Wenhao
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (48) : 13098 - 13101
  • [9] Diversity-Oriented Three-Component Reactions of Diazo Compounds with Anilines and 4-Oxo-Enoates
    Jing, Changcheng
    Xing, Dong
    Qian, Yu
    Shi, Taoda
    Zhao, Yun
    Hu, Wenhao
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) : 9289 - 9292
  • [10] Ternary Catalysis Enabled Three-Component Asymmetric Allylic Alkylation as a Concise Track to Chiral α,α-Disubstituted Ketones
    Kang, Zhenghui
    Chang, Wenju
    Tian, Xue
    Fu, Xiang
    Zhao, Wenxuan
    Xu, Xinfang
    Liang, Yong
    Hu, Wenhao
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (49) : 20818 - 20827