A new approach for an organocatalytic multicomponent domino asymmetric reaction

被引：226
|
作者：
Carlone, Armando [1 ]
Cabrera, Silvia [1 ]
Marigo, Mauro [1 ]
Jorgensen, Karl Anker [1 ]
机构：
[1] Aarhus Univ, Ctr Catalysis, Danish Natl Res Fdn, Dept Chem, DK-8000 Aarhus C, Denmark
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 07期
关键词：
aldehydes; asymmetry; domino reactions; multicomponent reactions; organocatalysis;
D O I：
10.1002/anie.200604479
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
As easy as pouring! Three C-C bonds, up to three stereocenters, and ee values greater than 97% are created in a new organocatalyzed multicomponent domino reaction (see picture; TMS = trimethylsilyl; EWG = electron-withdrawing group). Very high enantioselectivity, control of the substituents, easy handling, and user-friendly reaction conditions are key features of this transformation. (Figure Presented). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：1101 / 1104
页数：4
相关论文
共 50 条
  • [41] Organocatalytic Domino Reactions
    Alba, Andrea-Nekane
    Companyo, Xavier
    Viciano, Monica
    Rios, Ramon
    CURRENT ORGANIC CHEMISTRY, 2009, 13 (14) : 1432 - 1474
  • [42] Asymmetric Organocatalytic Four-Component Quadruple Domino Reaction Initiated by Oxa-Michael Addition of Alcohols to Acrolein
    Zhang, Fang-Lin
    Xu, Ai-Wen
    Gong, Yue-Fa
    Wei, Mo-Hui
    Yang, Xiang-Liang
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (28) : 6815 - 6818
  • [43] Organocatalytic Activation of Unsymmetrical 2,3-Diketones Towards Catalytic Asymmetric Domino Michael-Henry Reaction
    Wloszczak, Lukasz Adam
    Gorecki, Marcin
    Mlynarski, Jacek
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (35)
  • [44] A Branched Domino Reaction: Asymmetric Organocatalytic Two-Component Four-Step Synthesis of Polyfunctionalized Cyclohexene Derivatives
    Zeng, Xiaofei
    Ni, Qijian
    Raabe, Gerhard
    Enders, Dieter
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (10) : 2977 - 2980
  • [45] Organocatalytic asymmetric domino Michael-Henry reaction for the synthesis of substituted bicyclo[3.2.1]octan-2-ones
    Tsakos, Michail
    Elsegood, Mark R. J.
    Kokotos, Christoforos G.
    CHEMICAL COMMUNICATIONS, 2013, 49 (22) : 2219 - 2221
  • [46] An Asymmetric Organocatalytic Quadruple Domino Reaction Employing a Vinylogous Friedel-Crafts/Michael/Michael/Aldol Condensation Sequence
    Philipps, Arne R.
    Fritze, Lars
    Erdmann, Nico
    Enders, Dieter
    SYNTHESIS-STUTTGART, 2015, 47 (16): : 2377 - 2384
  • [47] Organocatalytic asymmetric synthesis of 2,4-disubstituted imidazolidines via domino addition-aza-Michael reaction
    Mukhopadhyay, Soumendranath
    Pan, Subhas Chandra
    CHEMICAL COMMUNICATIONS, 2018, 54 (08) : 964 - 967
  • [48] Mechanistic investigations of the asymmetric organocatalytic chlorocyclization reaction
    Marzijarani, Nastaran Salehi
    Ashtekar, Kumar
    Jaganathan, Arvind
    Marshall, Sarah
    Jackson, James E.
    Borhan, Babak
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [49] Organocatalytic asymmetric Michael reaction with acylsilane donors
    Wu, Lei
    Li, Guangxun
    Fu, Qingquan
    Yu, Luoting
    Tang, Zhuo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (03) : 443 - 447
  • [50] Organocatalytic asymmetric reaction cascade to substituted cyclohexylamines
    Zhou, Jian
    List, Benjamin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) : 7498 - +
12345