Lewis acid induced tandem Diels-Alder reaction/ring expansion as an equivalent of a [4+3] cycloaddition

被引：55
|
作者：
Davies, HML [1 ]
Dai, X [1 ]
机构：
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 09期
关键词：
D O I：
10.1021/ja039908q
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Aluminum chloride induced reaction between cyclopentadiene and α,β-unsaturated aldehydes results in the stereoselective formation of the products of a formal [4 + 3] cycloaddition. The reaction proceeds by a tandem Diels?Alder reaction/ring expansion. Copyright © 2004 American Chemical Society.
引用
收藏
页码：2692 / 2693
页数：2
相关论文
共 50 条
  • [31] LIBF4 - A MILD LEWIS ACID FOR INTRAMOLECULAR DIELS-ALDER REACTIONS
    SMITH, DA
    HOUK, KN
    TETRAHEDRON LETTERS, 1991, 32 (12) : 1549 - 1552
  • [32] Effect of substituents and promoters on the Diels-Alder cycloaddition reaction in the biorenewable synthesis of trimellitic acid
    Khan, Tuhin Suvra
    Gupta, Shelaka
    Ahmad, Maaz
    Alam, Md Imteyaz
    Haider, M. Ali
    RSC ADVANCES, 2020, 10 (51) : 30656 - 30670
  • [33] 3+2 Cycloaddition via a Diels-Alder retro-Diels-Alder sequence: Tandem cyclopentadienyl annulation of a 1,5-cyclooctadiyne synthetic equivalent.
    Davila, A
    Ramezanian, MS
    Fronczek, FR
    McLaughlin, ML
    TETRAHEDRON LETTERS, 1996, 37 (15) : 2517 - 2520
  • [34] A conceptual DFT approach towards analysing feasibility of the intramolecular cycloaddition Diels-Alder reaction of triene amide in Lewis acid catalyst
    ABDELILAH BENALLOU
    HABIB EL ALAOUI EL ABDALLAOUI
    HOCINE GARMES
    Journal of Chemical Sciences, 2016, 128 : 1489 - 1496
  • [35] Asymmetric Lewis acid organocatalysis of the Diels-Alder reaction by a silylated C-H acid
    Gatzenmeier, Tim
    van Gemmeren, Manuel
    Xie, Youwei
    Hoefler, Denis
    Leutzsch, Markus
    List, Benjamin
    SCIENCE, 2016, 351 (6276) : 949 - 952
  • [36] A conceptual DFT approach towards analysing feasibility of the intramolecular cycloaddition Diels-Alder reaction of triene amide in Lewis acid catalyst
    Benallou, Abdelilah
    El Abdallaoui, Habib El Alaoui
    Garmes, Hocine
    JOURNAL OF CHEMICAL SCIENCES, 2016, 128 (09) : 1489 - 1496
  • [37] COMPLEXES CONTAINING A LEWIS-ACID AND BRONSTED ACID FOR THE CATALYTIC ASYMMETRIC DIELS-ALDER REACTION
    AGGARWAL, VK
    ANDERSON, E
    GILES, R
    ZAPARUCHA, A
    TETRAHEDRON-ASYMMETRY, 1995, 6 (06) : 1301 - 1306
  • [38] Progress in Palladium-Catalyzed Diels-Alder [4+2] Cycloaddition Reaction
    Duan, Zebin
    Long, Yuhua
    Yang, Dingqiao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2010, 30 (03) : 368 - 380
  • [39] Lewis Acid Catalyzed Inverse-Electron-Demand Diels-Alder Reaction of Tropones
    Li, Pingfan
    Yamamoto, Hisashi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (46) : 16628 - +
  • [40] An efficient synthesis of chiral isoquinuclidines by Diels-Alder reaction using Lewis acid catalyst
    Hirama, Masafumi
    Kato, Yuji
    Seki, Chigusa
    Nakano, Hiroto
    Takeshita, Mitsuhiro
    Oshikiri, Noriko
    Iyoda, Masahiko
    Matsuyama, Haruo
    TETRAHEDRON, 2010, 66 (38) : 7618 - 7624
12345