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
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
下载
收藏
页码:2692 / 2693
页数:2
相关论文
共 50 条
  • [1] Formal enantioselective [4+3] cycloaddition by a tandem Diels-Alder reaction/ring expansion
    Dai, Xing
    Davies, Huw M. L.
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) : 2449 - 2456
  • [2] TANDEM CYCLOADDITION-ENZYMATIC TRANSESTERIFICATION - AN ENANTIOSELECTIVE DIELS-ALDER REACTION EQUIVALENT
    ANDREU, C
    MARCO, JA
    ASENSIO, G
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11): : 3209 - 3210
  • [3] Lewis acid-catalyzed tandem Diels-Alder reaction/retro-claisen rearrangement as an equivalent of the inverse electron demand hetero Diels-Alder reaction
    Davies, HML
    Dai, X
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17): : 6680 - 6684
  • [4] Lewis acid catalyst system for Diels-Alder reaction
    Kalepu, Rishir
    Mishra, Satyendra
    JOURNAL OF CHEMICAL SCIENCES, 2020, 132 (01)
  • [5] NEW LEWIS ACID CATALYSTS FOR THE DIELS-ALDER REACTION
    KELLY, TR
    MAITY, SK
    MEGHANI, P
    CHANDRAKUMAR, NS
    TETRAHEDRON LETTERS, 1989, 30 (11) : 1357 - 1360
  • [6] Lewis acid catalysis of a Diels-Alder reaction in water
    Otto, S
    Bertoncin, F
    Engberts, JBFN
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (33) : 7702 - 7707
  • [7] Enantioselective Diels-Alder cycloaddition by preorganization on a chiral Lewis acid template
    Bienaymé, H
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) : 2670 - 2673
  • [8] LEWIS ACID CATALYSIS OF A DIELS-ALDER CYCLOADDITION - AN UNDERGRADUATE ORGANIC EXPERIMENT
    MARCHAND, AP
    VIDYASAGAR, V
    BUCKNER, MB
    HOLMAN, PO
    JOURNAL OF CHEMICAL EDUCATION, 1987, 64 (07) : 642 - 644
  • [9] Stereoselective synthesis of the taxane ring system via the tandem Diels-Alder cycloaddition
    Winkler, JD
    Kim, HS
    Kim, S
    Ando, K
    Houk, KN
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (09): : 2957 - 2962
  • [10] LEWIS-ACID CATALYSIS OF A DIELS-ALDER REACTION IN WATER
    OTTO, S
    ENGBERTS, JBFN
    TETRAHEDRON LETTERS, 1995, 36 (15) : 2645 - 2648