Novel dipolarophiles and dipoles in the metal-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides

被引:385
|
作者
Adrio, Javier [1 ]
Carretero, Juan C. [1 ]
机构
[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain
关键词
ASYMMETRIC 3+2 CYCLOADDITION; NITRILE OXIDE CYCLOADDITIONS; DIVERSITY-ORIENTED SYNTHESIS; CHIRAL CALCIUM COMPLEXES; LEWIS-ACID; NITRONE CYCLOADDITIONS; BINAPHTHYLDIIMINE-NI(II) COMPLEXES; ALPHA; BETA-UNSATURATED ALDEHYDES; PYRROLIDINE DERIVATIVES; FULLERENE DERIVATIVES;
D O I
10.1039/c1cc10779h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides constitutes one of the most powerful and atom economical methods for the enantioselective construction of pyrrolidines. This article highlights the recent developments in this area, with special focus on contributions improving the structural scope at the dipolarophile and azomethine ylide partners.
引用
收藏
页码:6784 / 6794
页数:11
相关论文
共 50 条
  • [1] Recent advances in the enantioselective 1,3-dipolar cycloaddition of azomethine ylides and dipolarophiles
    Bdiri, Bilel
    Zhao, Boa-Jing
    Zhou, Zhi-Ming
    [J]. TETRAHEDRON-ASYMMETRY, 2017, 28 (07) : 876 - 899
  • [2] 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
    [J]. CHEMICAL COMMUNICATIONS, 2022, 58 (56) : 7805 - 7808
  • [3] Binap and Phosphoramidites as Privileged Chiral Ligands for the Metal-Catalyzed Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides
    Najera, Carmen
    Sansano, Jose M.
    [J]. CHEMICAL RECORD, 2016, 16 (06): : 2430 - 2448
  • [4] 1,3-Dipolar cycloaddition reactions of azomethine ylides with aromatic dipolarophiles
    Ryan, John H.
    [J]. ARKIVOC, 2015, : 160 - 183
  • [5] INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION OF STABILIZED AZOMETHINE YLIDES TO UNACTIVATED DIPOLAROPHILES
    HENKE, BR
    KOUKLIS, AJ
    HEATHCOCK, CH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26): : 7056 - 7066
  • [6] 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
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (32) : 9864 - 9873
  • [7] Ag/ThioClickFerrophos catalyzed highly enantioselective 1,3-dipolar cycloaddition of azomethine ylides with alkenes
    Shimizu, Kenta
    Ogata, Kenichi
    Fukuzawa, Shin-ichi
    [J]. TETRAHEDRON LETTERS, 2010, 51 (38) : 5068 - 5070
  • [8] Copper(I)-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides with vinyl sulfones
    Llamas, Tomas
    Gomez Arrayas, Ramon
    Carlos Carretero, Juan
    [J]. SYNTHESIS-STUTTGART, 2007, (06): : 950 - 956
  • [9] Catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides with vinyl sulfones
    Llamas, T
    Arrayás, RG
    Carretero, JC
    [J]. ORGANIC LETTERS, 2006, 8 (09) : 1795 - 1798
  • [10] Alkenyl Arenes as Dipolarophiles in Catalytic Asymmetric 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides
    Pascual-Escudero, Ana
    de Cozar, Abel
    Cossio, Fernando P.
    Adrio, Javier
    Carretero, Juan C.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (49) : 15334 - 15338