LEWIS ACID-CATALYZED HETERO-DIELS-ALDER REACTIONS OF METHYL 2-OXO-3-ALKENOATES WITH ALKENES

被引：17
|
作者：
SERA, A
OHARA, M
YAMADA, H
EGASHIRA, E
UEDA, N
SETSUNE, J
机构：
来源：
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1994年 / 67卷 / 07期
关键词：
D O I：
10.1246/bcsj.67.1912
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Lewis acid-catalyzed cycloadditions of 4-substituted methyl 2-oxo-3-butenoates and -3-pentenoates with alkenes took place with high regio- and stereoselectivities to afford substituted 6-methoxycarbonyl-3,4-dihydro-2H-pyrans in good to moderate yields. None of the ene products were produced. Similar reactions of methyl 3-phenyl-2-oxo-3-butenoate with alkenes afforded both the corresponding 3,4-dihydro-2H-pyrans and a dimeric cycloadduct of the diene component. The regio- and stereoselectivities of the present inverse-electron-demand cycloadditions indicated that the reactions proceeded through a concerted exo transition state.
引用
收藏
页码：1912 / 1917
页数：6
相关论文
共 50 条
  • [21] Asymmetric Hetero-Diels-Alder Reactions Catalyzed by Chiral Dirhodium (II) Complexes
    Anada, Masahiro
    Hashimoto, Shunichi
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2019, 77 (06) : 553 - 565
  • [22] The Origin of Catalysis and Regioselectivity of Lewis Acid-Catalyzed Diels-Alder Reactions with Tropone
    Tiekink, Eveline H. H.
    Vermeeren, Pascal
    Hamlin, Trevor A. A.
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (39)
  • [23] Origin of enantioselection in hetero-Diels-Alder reactions catalyzed by naphthyl-TADDOL
    Anderson, Christopher D.
    Dudding, Travis
    Gordillo, Ruth
    Houk, K. N.
    ORGANIC LETTERS, 2008, 10 (13) : 2749 - 2752
  • [24] (E)-2-OXO-1-SULFONYL-3-ALKENES AS REACTIVE HETERO 1,3-DIENES - ABSOLUTELY ENDO-SELECTIVE HETERO-DIELS-ALDER REACTIONS WITH VINYL ETHERS IN THE PRESENCE OF A LEWIS-ACID CATALYST
    WADA, E
    YASUOKA, H
    KANEMASA, S
    CHEMISTRY LETTERS, 1994, (01) : 145 - 148
  • [25] Theoretical study on the hetero-Diels-Alder reactions between methyl pyridinedithiocarboxylates and butadienes
    Wang Yan
    Fang De-Cai
    Liu Ruo-Zhuang
    ACTA CHIMICA SINICA, 2007, 65 (18) : 1987 - 1994
  • [26] Internally Lewis acid-catalyzed Diels-Alder cycloadditions
    Bienayme, H
    Longeau, A
    TETRAHEDRON, 1997, 53 (28) : 9637 - 9646
  • [27] Competition between Diels-Alder and hetero-Diels-Alder reactions: The effect of Lewis acid catalysis on unsymmetrical bifurcating potential energy surface
    Celebi-Olcum, Nihan
    Aviyente, Viktorya
    Houk, K. N.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [28] ACID-CATALYZED DIELS-ALDER REACTIONS OF CYCLOALKENONES
    FRINGUELLI, F
    PIZZO, F
    TATICCHI, A
    WENKERT, E
    SYNTHETIC COMMUNICATIONS, 1979, 9 (05) : 391 - 394
  • [29] Heteropoly acid-catalyzed Diels-Alder reactions
    G.J. Meuzelaar
    L. Maat
    R.A. Sheldon
    I.V. Kozhevnikov
    Catalysis Letters, 1997, 45 : 249 - 251
  • [30] Peri- and enantioselectivity of thermal, scandium-, and [pybox/scandium]-catalyzed diels-alder and hetero-Diels-Alder reactions of methyl (E)-2-oxo-4-aryl-butenoates with cyclopentadiene
    Desimoni, Giovanni
    Faita, Giuseppe
    Toscanini, Marco
    Boiocchi, Massimo
    CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (34) : 9478 - 9485
12345