Organocatalytic Activation of Polycyclic Aromatic Compounds for Asymmetric Diels-Alder Reactions

被引：68
|
作者：
Jiang, Hao [1 ]
Rodriguez-Escrich, Carles [1 ]
Johansen, Tore Kiilerich [1 ]
Davis, Rebecca L. [1 ]
Jorgensen, Karl Anker [1 ]
机构：
[1] Aarhus Univ, Dept Chem, DK-8000 Aarhus C, Denmark
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 41期
关键词：
anthracene activation; aromaticity; asymmetric catalysis; Diels-Alder reaction; organocatalysis; BETA-SULFONYLNITROOLEFINS; NITRO-COMPOUNDS; ANTHRACENE; CATALYSIS; DERIVATIVES; ANTHRONES; TETRACYANOETHYLENE; REGIOSELECTIVITY; TRANSFORMATIONS; THERMOCHEMISTRY;
D O I：
10.1002/anie.201205836
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The anglerfish catalyst: The activation of anthracenes through aminocatalysis (see scheme) allows them to undergo [4+2] cycloadditions with concomitant breaking of the aromaticity at room temperature and low catalyst loadings. A highly enantioselective Diels-Alder reaction of anthracenes has been developed using nitroalkenes as dienophiles. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：10271 / 10274
页数：4
相关论文
共 50 条
  • [1] Asymmetric organocatalytic Diels-Alder reactions on solid support
    Selkälä, SA
    Tois, J
    Pihko, PM
    Koskinen, AMP
    ADVANCED SYNTHESIS & CATALYSIS, 2002, 344 (09) : 941 - 945
  • [2] The Diels-Alder Reaction for the Synthesis of Polycyclic Aromatic Compounds
    Dyan, Ok Ton
    Borodkin, Gennady I.
    Zaikin, Pavel A.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (44) : 7271 - 7306
  • [3] Organocatalytic Asymmetric Diels-Alder Reactions of 3-Vinylindoles
    Gioia, Claudio
    Hauville, Agnes
    Bernardi, Luca
    Fini, Francesco
    Ricci, Alfredo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (48) : 9236 - 9239
  • [4] DIELS-ALDER REACTIONS INVOLVING AZONIA POLYCYCLIC AROMATIC COMPOUNDS AND NUCLEOPHILIC DIENOPHILES
    FIELDS, DL
    REGAN, TH
    DIGNAN, JC
    JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (01): : 390 - &
  • [5] Organocatalytic asymmetric Diels-Alder reactions with novel chiral hydrazines
    Cook, Gregory R.
    Vaughn, Danielle
    Bhor, Santosh
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [6] Dual Activation of Aromatic Diels-Alder Reactions
    Narsaria, Ayush K.
    Hamlin, Trevor A.
    Lammertsma, Koop
    Bickelhaupt, F. Matthias
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (42) : 9902 - 9912
  • [7] Enantioselective Organocatalytic Diels-Alder Reactions
    Merino, Pedro
    Marques-Lopez, Eugenia
    Tejero, Tomas
    Herrera, Raquel P.
    SYNTHESIS-STUTTGART, 2010, (01): : 1 - 26
  • [8] DIELS-ALDER REACTIONS OF TETRAFLUOROBENZYNE WITH AROMATIC AND HETEROAROMATIC COMPOUNDS
    CALLANDER, DD
    COE, PL
    TATLOW, JC
    CHEMICAL COMMUNICATIONS, 1966, (05) : 143 - +
  • [9] Asymmetric Synthesis of Nature-Inspired Bioactive Spiro Compounds through Organocatalytic Diels-Alder Reactions
    Ramachary, Dhevalapally B.
    Krishna, Patoju M.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (06) : 729 - 734
  • [10] Direct Access to Multifunctionalized Norcamphor Scaffolds by Asymmetric Organocatalytic Diels-Alder Reactions
    Mose, Rasmus
    Jensen, Magnus E.
    Preegel, Gert
    Jorgensen, Karl Anker
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (46) : 13630 - 13634
12345