Enantioselective Catalytic [3+3] Cycloaddition of Donor-Acceptor Aziridines with m-N,N-Dialkylaminophenyl Methylidenemalonates

被引:2
|
作者
Kim, Sung-Gon [1 ]
机构
[1] Kyonggi Univ, Dept Chem, Suwon 16227, South Korea
来源
BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2019年 / 40卷 / 07期
关键词
Cycloaddition; Asymmetric catalysis; Donor-acceptor aziridine; Tetrahydroisoquinoline; ASYMMETRIC-SYNTHESIS; N-TOSYLAZIRIDINES; CYCLOPROPANE 1,1-DIESTERS; ALDEHYDES; 1,2,3,4-TETRAHYDROISOQUINOLINES; N; N-DIALKYL-3-VINYLANILINES; OXAZOLIDINES; ANNULATION; CARBONYLS; CLEAVAGE;
D O I
10.1002/bkcs.11758
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Copper(I)-catalyzed cyclization reactions of ethyl (E)-alpha-ethynyl-beta-aryl-alpha,beta-unsaturated esters with N-sulfonyl azides for the synthesis of 1-aminonaphthalenes, 3-aminobenzofurans, and 3-aminothiobenzofurans.
引用
收藏
页码:747 / 750
页数:4
相关论文
共 50 条
  • [1] Asymmetric [3+3] Cycloaddition of Donor-Acceptor Aziridines with N,N-Dialkyl-3-vinylanilines to Construct Highly Functionalized Enantioenriched Tetrahydroisoquinolines
    Kim, Seungyeon
    Kim, Sung-Gon
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (09) : 1621 - 1625
  • [2] Stereoselective Cascade Reactions of Donor-Acceptor Cyclopropanes with m-N,N-Dialkylaminophenyl α,β-Unsaturated Carbonyls: Diastereoselective Synthesis of cis- and trans-Tetralins
    Sin, Seunghui
    Kim, Sung-Gon
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (16) : 2701 - 2706
  • [3] Enantioselective Synthesis of Azetidines through [3+1]-Cycloaddition of Donor-Acceptor Aziridines with Isocyanides
    Zhang, Fengcai
    Sang, Xinpeng
    Zhou, Yuqiao
    Cao, Weidi
    Feng, Xiaoming
    ORGANIC LETTERS, 2022, 24 (07) : 1513 - 1517
  • [4] Asymmetric [3+n]-Cycloaddition Reactions of Donor-Acceptor Cyclopropanes
    Bao, Ming
    Doyle, Michael P.
    CHEMCATCHEM, 2023, 15 (23)
  • [5] A donor-acceptor cyclopropene as a dipole source for a silver(I) catalyzed asymmetric catalytic [3+3]-cycloaddition with nitrones
    Xu, Xinfang
    Zavalij, Peter J.
    Doyle, Michael P.
    CHEMICAL COMMUNICATIONS, 2013, 49 (87) : 10287 - 10289
  • [6] Lewis acid-catalyzed [3+3] cycloadditions of donor-acceptor aziridines with N,N-dialkyl-3-vinylanilines via carbon-carbon bond cleavage
    Lee, Sang Gyu
    Kim, Sung-Gon
    TETRAHEDRON, 2018, 74 (27) : 3671 - 3678
  • [7] Enantioselective [3+2] Cycloaddition of Donor-Acceptor Aziridines and Imines to Construct 2,5-trans-Imidazolidines
    Qiao, Jianglin
    Wang, Shiyu
    Liu, Xiaohua
    Feng, Xiaoming
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (18)
  • [8] (3+3)-Annulation of Donor-Acceptor Cyclopropanes with Diaziridines
    Chagarovskiy, Alexey O.
    Vasin, Vladimir S.
    Kuznetsov, Vladimir V.
    Ivanova, Olga A.
    Rybakov, Victor B.
    Shumsky, Alexey N.
    Makhova, Nina N.
    Trushkov, Igor V.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (32) : 10338 - 10342
  • [9] [3+3]-Cycloaddition of Donor-Acceptor Cyclopropanes with Nitrile Imines Generated in Situ: Access to Tetrahydropyridazines
    Garve, Lennart K. B.
    Petzold, Martin
    Jones, Peter G.
    Werz, Daniel B.
    ORGANIC LETTERS, 2016, 18 (03) : 564 - 567
  • [10] Lewis Acid/Rhodium-Catalyzed Formal [3+3]-Cycloaddition of Enoldiazoacetates with Donor-Acceptor Cyclopropanes
    Cheng, Qing-Qing
    Qian, Yu
    Zavalij, Peter Y.
    Doyle, Michael P.
    ORGANIC LETTERS, 2015, 17 (14) : 3568 - 3571