Organocatalytic Asymmetric Triple Domino Reactions of Nitromethane with α,β-Unsaturated Aldehydes

被引：38
|
作者：
Enders, Dieter [1 ]
Jeanty, Matthieu [1 ]
Bats, Jan W. [2 ]
机构：
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
[2] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60439 Frankfurt, Germany
来源：
SYNLETT | 2009年 / 19期
关键词：
domino reaction; organocatalysis; Michael addition; nitroalkane; aldol condensation; ENANTIOSELECTIVE CONJUGATE ADDITION; TRICYCLIC CARBON FRAMEWORKS; MICHAEL ADDITION; NITROALKANES; ENONES; CATALYST; KETONES; AMINOCATALYSIS; ACTIVATION; STRATEGIES;
D O I：
10.1055/s-0029-1218282
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An organocatalytic asymmetric multicomponent domino reaction employing the bulk chemical nitromethane and alpha,beta-unsaturated aldehydes as substrates is described. The new triple cascade reaction based on two subsequent Michael additions and an intramolecular aldol condensation provides an atom-economic entry to diastereo- and enantiomerically pure 5-nitrocyclohexene carbaldehydes after flash chromatography.
引用
收藏
页码：3175 / 3178
页数：4
相关论文
共 50 条
  • [21] Asymmetric synthesis of highly functionalized tetrahydrothiophenes by organocatalytic domino reactions
    Brandau, Sven
    Maerten, Eddy
    Jorgensen, Karl Anker
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) : 14986 - 14991
  • [22] Asymmetric Organocatalytic Tandem/Domino Reactions to Access Bioactive Products
    Pellissier, Helene
    CURRENT ORGANIC CHEMISTRY, 2021, 25 (13) : 1457 - 1471
  • [23] Organocatalytic enantioselective conjugate addition-cyclization domino reactions of o-N-protected aminophenyl α,β-unsaturated aldehydes
    Heo, Seungpyeong
    Kim, Shinae
    Kim, Sung-Gon
    TETRAHEDRON LETTERS, 2013, 54 (36) : 4978 - 4981
  • [24] Organocatalytic enantioselective Michael addition reactions of fluoromalonates with α,β-unsaturated aldehydes
    Li Hao
    Ji YaFei
    Li Jian
    Zhang ShiLei
    Yu ChenGuang
    Wang Wei
    SCIENCE CHINA-CHEMISTRY, 2010, 53 (01) : 135 - 139
  • [25] Organocatalytic enantioselective Michael addition reactions of fluoromalonates with α,β-unsaturated aldehydes
    Hao Li
    YaFei Ji
    Jian Li
    ShiLei Zhang
    ChenGuang Yu
    Wei Wang
    Science China Chemistry, 2010, 53 : 135 - 139
  • [26] Organocatalytic enantioselective Michael addition reactions of fluoromalonates with α,β-unsaturated aldehydes
    LI HaoJI YaFeiLI JianZHANG ShiLeiYU ChenGuang WANG Wei Department of Chemistry and Chemical BiologyUniversity of New MexicoAlbuquerqueNM USA Department of Pharmaceutical SciencesSchool of PharmacyEast China University of Science and TechnologyShanghai China
    Science China(Chemistry), 2010, 53 (01) : 135 - 139
  • [27] Organocatalytic enantioselective Michael addition reactions of fluoromalonates with α,β-unsaturated aldehydes
    LI Hao1
    2 Department of Pharmaceutical Sciences
    Science China(Chemistry), 2010, (01) : 135 - 139
  • [28] Organocatalytic asymmetric hydrophosphination of α,β-unsaturated aldehydes:: Development, mechanism and DFT calculations
    Ibrahem, Ismail
    Hammar, Peter
    Vesely, Jan
    Rios, Ramon
    Eriksson, Lars
    Cordova, Armando
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (11-12) : 1875 - 1884
  • [29] Asymmetric organocatalytic oxy-Michael addition of alcohols to α,β-unsaturated aldehydes
    Kano, Taichi
    Tanaka, Youhei
    Maruoka, Keiji
    TETRAHEDRON, 2007, 63 (35) : 8658 - 8664
  • [30] Metal-free, organocatalytic asymmetric transfer hydrogenation of α,β-unsaturated aldehydes
    Yang, JW
    Fonseca, MTH
    Vignola, N
    List, B
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (01) : 108 - 110
12345