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
  • [21] 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
  • [22] Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides
    Najera, Carmen
    Miguel Sansano, Jose
    PURE AND APPLIED CHEMISTRY, 2019, 91 (04) : 575 - 596
  • [23] Silver Acetate/TF-BiphamPhos-Catalyzed endo-Selective Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides with Vinyl Phenyl Sulfone
    Liang, Gang
    Tong, Min-Chao
    Wang, Chun-Jiang
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) : 3101 - 3106
  • [24] 1,3-dipolar cycloaddition reactions of benzo[b]thiophene 1,1-dioxide with azomethine ylides
    Malatesti, Nela
    Boa, Andrew N.
    Clark, Stephen
    Westwood, Robert
    TETRAHEDRON LETTERS, 2006, 47 (29) : 5139 - 5142
  • [25] 1,3-Dipolar Cycloaddition of Polycyclic Aromatic Azomethine Ylides and Alkynylbenziodoxoles for Synthesis of Functional Dibenzoullazines
    Han, Hui
    Goh, Glen Wee Zhuan
    Li, Yongxin
    Yoshikai, Naohiko
    Ito, Shingo
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (10) : 1079 - 1083
  • [26] Synthesis of Pyrrole-Fused Corannulenes: 1,3-Dipolar Cycloaddition of Azomethine Ylides to Corannulene
    Tokimaru, Yuki
    Ito, Shingo
    Nozaki, Kyoko
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (49) : 15560 - 15564
  • [27] Application of 1,3-Dipolar Reactions between Azomethine Ylides and Alkenes to the Synthesis of Catalysts and Biologically Active Compounds
    Arrastia, Iosune
    Arrieta, Ana
    Cossio, Fernando P.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (43) : 5889 - 5904
  • [28] Binap-Gold(I) versus Binap-Silver Trifluoroacetate Complexes as Catalysts in 1,3-Dipolar Cycloadditions of Azomethine Ylides
    Martin-Rodriguez, Maria
    Najera, Carmen
    Sansano, Jose M.
    de Cozar, Abel
    Cossio, Fernando P.
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (50) : 14224 - 14233
  • [29] Synthetic applications of 1,3-dipolar cycloaddition of azomethine ylides and use in molecular nanotechnology
    Sharma, Kusum
    Shrivastava, Barkha
    Prashant, Anita
    Joshi, Rahul
    Pardasani, R. T.
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2014, 91 (08) : 1411 - 1417
  • [30] The first example of the generation of azomethine ylides from a fluorocarbene: 1,3-cyclization and 1,3-dipolar cycloaddition
    Konev, AS
    Novikov, MS
    Khlebnikov, AF
    TETRAHEDRON LETTERS, 2005, 46 (48) : 8337 - 8340