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
来源：
SYNLETT | 2010年 / 16期
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
  • [31] Stereoselective Synthesis of Functionalized Cyclopropane Derivatives via α-Thiocyanate Ketone-Based Three-Component Reaction
    Wu, Fei-Yue
    Li, Ying
    Feng, Hui
    Wu, Qiong
    Jiang, Bo
    Shi, Feng
    Tu, Shu-Jiang
    SYNTHESIS-STUTTGART, 2011, (15): : 2459 - 2465
  • [32] Three-component Synthesis of Novel Highly Functionalized 2,6-dihydropyrimido[2,1-a]isoindole Derivatives
    Baharfar, Robabeh
    Abbasi, Najmeh
    ACTA CHIMICA SLOVENICA, 2011, 58 (04) : 840 - 845
  • [33] Three-component synthesis of functionalized 4,5,6,7-tetrahydroindole derivatives
    A. V. Andina
    A. N. Andin
    Russian Journal of Organic Chemistry, 2015, 51 : 1043 - 1045
  • [34] Three-component synthesis of functionalized 4,5,6,7-tetrahydroindole derivatives
    Andina, A. V.
    Andin, A. N.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 51 (07) : 1043 - 1045
  • [35] Regioselective synthesis of functionalized [1,8]-naphthyridine derivatives via three-component domino reaction under catalyst-free conditions
    Feng, Xian
    Wang, Jian-Jun
    Zhang, Juan-Juan
    Cao, Cheng-Pao
    Huang, Zhi-Bin
    Shi, Da-Qing
    GREEN CHEMISTRY, 2015, 17 (02) : 973 - 981
  • [36] A Sakurai-Prins-Ritter sequence for the three-component diastereoselective synthesis of 4-amino tetrahydropyrans
    Epstein, Oleg L.
    Rovis, Tomislav
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (51) : 16480 - 16481
  • [37] Synthesis of functionalized nitrocyclohexene derivatives from 2-nitrocycloalkanones, via anionic domino reactions
    Ballini, R
    Barboni, L
    Bosica, G
    Fiorini, D
    Gil, MV
    Petrini, M
    TETRAHEDRON, 2001, 57 (28) : 6079 - 6081
  • [38] Three-component domino reaction in Triton B: A facile synthesis of 4H-chromene derivatives
    Talukdar, Mrinal
    Islam, Nasreen
    Begari, Eeshwaraiah
    RESULTS IN CHEMISTRY, 2023, 6
  • [39] One-pot, three-component synthesis of highly functionalized 1,3-oxazine derivatives from α,β-unsaturated imine, alkyne, and aldehyde
    Lei, Ming
    Zhan, Zujin
    Tian, Wan
    Lu, Ping
    TETRAHEDRON, 2012, 68 (16) : 3361 - 3367
  • [40] A Rh-catalyzed three-component reaction for the diastereoselective synthesis of pyrazolone derivatives with contiguous quaternary stereocenters
    Ao, Chaoqun
    Huang, Jingjing
    Xu, Xinfang
    Jia, Shikun
    Kang, Zhenghui
    Hu, Wenhao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (18) : 3466 - 3470
12345