Catalytic enantioselective 1,3-dipolar cycloaddition reactions of azomethine ylides and alkenes by using phosphoramidite-silver(I) complexes

被引:113
|
作者
Najera, Carmen [1 ]
Retamosa, M. de Gracia [1 ]
Sansano, Jose M. [1 ]
机构
[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain
关键词
azomethine ylides; chirality; cycloaddition; phosphoramidites; silver;
D O I
10.1002/anie.200801690
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Presented) Silver catalysts: A novel chiral phosphoramidite -silver perchlorate complex has been used for the synthesis of highly substituted pyrolidine rings. This method is valuable for the synthesis of biologically active α-substituted prolines by using hindered dipoles generated from α-substituted α amino acids (see scheme; DABCO=1,4-diazabicyclo[2.2.2]octane). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6055 / 6058
页数:4
相关论文
共 50 条
  • [31] Auxiliary controlled intramolecular 1,3-dipolar cycloaddition reactions of chiral azomethine ylides
    Dogan, Ö
    Garner, PP
    TURKISH JOURNAL OF CHEMISTRY, 2000, 24 (01): : 59 - 66
  • [32] Catalytic enantioselective inverse-electron demand 1,3-dipolar cycloaddition reactions of nitrones with alkenes
    Simonsen, KB
    Bayón, P
    Hazell, RG
    Gothelf, KV
    Jorgensen, KA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (16) : 3845 - 3853
  • [33] Diastereoselective 1,3-dipolar cycloaddition of cyclopropenes to acenaphthenequinone azomethine ylides
    Stepakov, Alexander, V
    Pronina, Yulia A.
    Filatov, Alexander S.
    Selivanov, Stanislav I.
    Kornev, Anton A.
    Kryukova, Mariya A.
    Ponyaev, Alexander I.
    Boitsov, Vitali M.
    TETRAHEDRON, 2024, 151
  • [34] Unprecedented 1,3-dipolar cycloaddition of azomethine ylides to ester carbonyl
    Novikov, MS
    Voznyi, IV
    Khlebnikov, AF
    Kopf, J
    Kostikov, RR
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (14): : 1628 - 1630
  • [35] Diastereoselective Silver-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with Fluorinated Imine
    Xie, Haibo
    Zhu, Jiangtao
    Chen, Zixian
    Li, Shan
    Wu, Yongming
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21): : 7468 - 7471
  • [36] DIASTEREOFACIAL SELECTIVITY IN THE 1,3-DIPOLAR CYCLOADDITION OF CHIRAL AZOMETHINE YLIDES
    DEPREZ, P
    ROUDEN, J
    CHIARONI, A
    RICHE, C
    ROYER, J
    HUSSON, HP
    TETRAHEDRON LETTERS, 1991, 32 (51) : 7531 - 7534
  • [37] INFLUENCE OF AG(I) AND LI(I) CATALYSTS FOR 1,3-DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE YLIDES - REVERSAL OF THE STEREOCHEMISTRY
    NYERGES, M
    RUDAS, M
    TOTH, G
    HERENYI, B
    KADAS, I
    BITTER, I
    TOKE, L
    TETRAHEDRON, 1995, 51 (48) : 13321 - 13330
  • [38] Stereochemical diversity in pyrrolidine synthesis by catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides
    Adrio, Javier
    Carretero, Juan C.
    CHEMICAL COMMUNICATIONS, 2019, 55 (80) : 11979 - 11991
  • [39] Synthesis of Spirocyclic Amines by 1,3-Dipolar Cycloaddition of Azomethine Ylides and Azomethine Imines
    Choi, Anthony
    Castle, Jemma
    Saruengkhanphasit, Rungroj
    Coldham, Iain
    SYNTHESIS-STUTTGART, 2020, 52 (08): : 1273 - 1278
  • [40] 1,3-dipolar cycloaddition reactions of stable bicyclic and monocyclic azomethine ylides:: Preparative aspects
    Elender, K
    Nöth, H
    Riebel, P
    Weber, A
    Sauer, J
    TETRAHEDRON, 2000, 56 (30) : 5443 - 5463