Three-Component, Diastereoselective Synthesis of Highly Functionalized Indane Derivatives Based on an Anionic Domino Sequence from α-Nitroketones

被引:12
|
作者
Giorgi, Giorgio [1 ]
Arroyo, Francisco J. [1 ]
Lopez-Alvarado, Pilar [1 ]
Carlos Menendez, J. [1 ]
机构
[1] Univ Complutense, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain
关键词
carbocycles; domino reactions; nitroketones; carbanions; nitroaldol reactions; DIVERSITY-ORIENTED SYNTHESIS; POTENT INHIBITORS; CHEMISTRY; STRATEGY; PART;
D O I
10.1055/s-0030-1258048
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction between seven- or eight-membered cyclic alpha-nitroketones and aromatic 1,2-dialdehydes in the presence of DBU, with tetrahydrofuran containing some water as solvent, afforded 2-nitroindane-1,2-diols with three contiguous stereocenters, one of which is quaternary, in a one-pot, diastereoselective fashion.
引用
收藏
页码:2465 / 2467
页数:3
相关论文
共 50 条
  • [21] A highly regioselective synthesis of functionalized furo[3,2-a]acridine derivatives via a three-component reaction
    Yan Zhang
    Jing Xu
    Mei-Mei Zhang
    Xiang-Shan Wang
    Research on Chemical Intermediates, 2015, 41 : 9917 - 9927
  • [22] A highly regioselective synthesis of functionalized furo[3,2-a]acridine derivatives via a three-component reaction
    Zhang, Yan
    Xu, Jing
    Zhang, Mei-Mei
    Wang, Xiang-Shan
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (12) : 9917 - 9927
  • [23] Efficient synthesis of highly functionalized tetrahydropyridopyrimidines by a novel three-component coupling reaction
    Raheem, Izzat T.
    Schreier, John D.
    Breslin, Michael J.
    TETRAHEDRON LETTERS, 2011, 52 (30) : 3849 - 3852
  • [24] Synthesis of highly functionalized thiophenes by three-component and one-pot reaction
    Hassanabadi, Alireza
    Hosseini-Tabatabaei, Mohammad R.
    JOURNAL OF SULFUR CHEMISTRY, 2012, 33 (03) : 273 - 277
  • [25] Facile synthesis of highly functionalized stable ketenimines via a three-component reaction
    Alizadch, Abdolali
    Rostamnia, Sadegh
    SYNTHESIS-STUTTGART, 2008, (01): : 57 - 60
  • [26] A Highly Diastereoselective Three-component Domino Reaction in Water Yielding Poly-substituted 4,5-Dihydropyrroles
    Tong, Guangjing
    Xu, Haiwei
    Fan, Wei
    Jiang, Bo
    Wang, Shuliang
    Tu, Shujiang
    CHINESE JOURNAL OF CHEMISTRY, 2013, 31 (08) : 1039 - 1044
  • [27] N-Heterocyclic carbene-catalyzed (NHC) three-component domino reactions: highly stereoselective synthesis of functionalized acyclic ε-ketoesters
    Ma, Jianze
    Huang, You
    Chen, Ruyu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (06) : 1791 - 1798
  • [28] L-Proline-catalyzed three-component domino reactions for the synthesis of highly functionalized pyrazolo[3,4-b]pyridines
    Gunasekaran, Pethaiah
    Prasanna, Pitchaimani
    Perumal, Subbu
    TETRAHEDRON LETTERS, 2014, 55 (02) : 329 - 332
  • [29] Functionalized imidazoliniums from the three-component domino reaction of N-formylmethylcarboxamides with amines and isocyanides
    Lei, Chuan-Hu
    Zhao, Liang
    Wang, De-Xian
    Zhu, Jieping
    Wang, Mei-Xiang
    ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (08): : 909 - 913
  • [30] A Highly Diastereoselective Synthesis of α-Hydroxy-β-amino Acid Derivatives via a Lewis Acid Catalyzed Three-Component Condensation Reaction
    Gassa, Federico
    Contini, Alessandro
    Fontana, Gabriele
    Pellegrino, Sara
    Gelmi, Maria Luisa
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21): : 7099 - 7106