Unprecedented 1,3-dipolar cycloaddition of azomethine ylides to ester carbonyl

被引:25
|
作者
Novikov, MS
Voznyi, IV
Khlebnikov, AF
Kopf, J
Kostikov, RR
机构
[1] St Petersburg State Univ, Dept Chem, St Petersburg 198504, Russia
[2] Univ Hamburg, Inst Inorgan Chem, D-20146 Hamburg, Germany
关键词
D O I
10.1039/b204464a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Fluorinated azomethine ylides generated by the reaction of difluorocarbene with aryl and alkyl imines of O-acylated salicylaldehyde undergo intramolecular 1,3-dipolar cyclo-addition across the ester carbonyl to give 2,8-dioxa-6- azabicyclo[3.2.1]octane derivatives.
引用
下载
收藏
页码:1628 / 1630
页数:3
相关论文
共 50 条
  • [21] First Example of 1,3-Dipolar Cycloaddition of Carbonyl Ylides to Cyclopropenes
    A. P. Molchanov
    V. V. Diev
    J. Kopf
    R. R. Kostikov
    Russian Journal of Organic Chemistry, 2004, 40 : 431 - 433
  • [22] First example of 1,3-dipolar cycloaddition of carbonyl ylides to cyclopropenes
    Molchanov, AP
    Diev, VV
    Kopf, J
    Kostikov, RR
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (03) : 431 - 433
  • [23] Catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides with vinyl sulfones
    Llamas, T
    Arrayás, RG
    Carretero, JC
    ORGANIC LETTERS, 2006, 8 (09) : 1795 - 1798
  • [24] Recent advances in the enantioselective 1,3-dipolar cycloaddition of azomethine ylides and dipolarophiles
    Bdiri, Bilel
    Zhao, Boa-Jing
    Zhou, Zhi-Ming
    TETRAHEDRON-ASYMMETRY, 2017, 28 (07) : 876 - 899
  • [25] 1,3-dipolar cycloaddition of fluorinated azomethine ylides at the C=N bond
    M. S. Novikov
    A. F. Khlebnikov
    M. A. Egarmin
    J. Kopf
    R. R. Kostikov
    Russian Journal of Organic Chemistry, 2004, 40 : 1493 - 1499
  • [26] Recent advances in the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides
    Adrio, Javier
    Carretero, Juan C.
    CHEMICAL COMMUNICATIONS, 2014, 50 (83) : 12434 - 12446
  • [27] POLYFUNCTIONALIZED PYRROLIDINES BY STEREOSELECTIVE 1,3-DIPOLAR CYCLOADDITION OF AZOMETHINE YLIDES TO CHIRAL ENONES
    GALLEY, G
    LIEBSCHER, J
    PATZEL, M
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (16): : 5005 - 5010
  • [28] Pyrrole and Oligopyrrole Synthesis by 1,3-Dipolar Cycloaddition of Azomethine Ylides with Sulfonyl Dipolarophiles
    Robles-Machin, Rocio
    Lopez-Perez, Ana
    Gonzalez-Esguevillas, Maria
    Adrio, Javier
    Carlos Carretero, Juan
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (32) : 9864 - 9873
  • [29] Catalytic enantioselective intramolecular 1,3-dipolar cycloaddition of azomethine ylides with fluorinated dipolarophiles
    Cristobal, Christian
    Gavina, Daniel
    Alonso, Ines
    Ribagorda, Maria
    Carretero, Juan C.
    del Pozo, Carlos
    Adrio, Javier
    CHEMICAL COMMUNICATIONS, 2022, 58 (56) : 7805 - 7808
  • [30] Asymmetric Organocatalytic 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-Substituted Cyclic Enones
    Zhong, Han
    Zhang, Xiao-Yi
    Yao, Yong-Mou
    Chen, Wen-Ming
    Wang, Wei
    Tian, Xu
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (14): : 9721 - 9732