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
  • [21] Organocatalytic asymmetric Mannich reaction
    Ma Jingjun
    Li Ning
    Wu Qiuhua
    Zhou Xin
    Zang Xiaohuan
    Wang Chun
    PROGRESS IN CHEMISTRY, 2008, 20 (01) : 76 - 86
  • [22] Organocatalytic Asymmetric Triple Domino Reactions of Nitromethane with α,β-Unsaturated Aldehydes
    Enders, Dieter
    Jeanty, Matthieu
    Bats, Jan W.
    SYNLETT, 2009, (19) : 3175 - 3178
  • [23] 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
  • [24] Asymmetric Organocatalytic Tandem/Domino Reactions to Access Bioactive Products
    Pellissier, Helene
    CURRENT ORGANIC CHEMISTRY, 2021, 25 (13) : 1457 - 1471
  • [25] Asymmetric Synthesis of Fully Substituted Cyclopentane-Oxindoles through an Organocatalytic Triple Michael Domino Reaction
    Zou, Liang-Hua
    Philipps, Arne R.
    Raabe, Gerhard
    Enders, Dieter
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (03) : 1004 - 1008
  • [26] Construction of Chiral Multi-Functionalized Polyheterocyclic Benzopyran Derivatives by Using an Asymmetric Organocatalytic Domino Reaction
    Guo, Zhi-Wei
    Li, Xin-Sheng
    Zhu, Wei-Dong
    Xie, Jian-Wu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (35) : 6924 - 6932
  • [27] Organocatalytic Enantioselective Construction of Spiroketal Lactones Bearing Axial and Central Chirality via an Asymmetric Domino Reaction
    Xu, Shiyu
    Huang, Aima
    Yang, Yang
    Wang, Ying
    Zhang, Ming
    Sun, Zhihui
    Zhao, Man
    Wei, Yuanlin
    Li, Guofeng
    Hong, Liang
    ORGANIC LETTERS, 2022, 24 (16) : 2978 - 2982
  • [28] Asymmetric Synthesis of Functionalized Dihydro- and Tetrahydropyrans via an Organocatalytic Domino Michael-Hemiacetalization Reaction
    Urbanietz, Gregor
    Atodiresei, Iuliana
    Enders, Dieter
    SYNTHESIS-STUTTGART, 2014, 46 (09): : 1261 - 1269
  • [29] Multicomponent Domino Reaction in the Asymmetric Synthesis of Cyclopentan[c]pyran Core of Iridoid Natural Products
    Manchado, Alejandro
    Elena Ramos, Victoria
    Diez, David
    Garrido, Narciso M.
    MOLECULES, 2020, 25 (06):
  • [30] Organocatalytic Diastereoselective Multicomponent Domino Knoevenagel/Diels-Alder Reaction: Synthesis of Densely Functionalized Spiro[5.5]undecane
    Liu, Pan
    Chen, Duoyuan
    Zhang, Shouyue
    Zhou, Rui
    Ren, Wen
    Ouyang, Liang
    He, Gu
    CURRENT ORGANIC SYNTHESIS, 2015, 12 (01) : 88 - 94
12345