Masked Ketenes as Dienophiles in the Diels-Alder Reaction

被引:8
|
作者
Mackay, Emily G. [1 ]
Newton, Christopher G. [2 ]
机构
[1] Westfal Wilhelms Univ, Organ Chem Inst, Corrensstr 40, D-48149 Munster, Germany
[2] Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Asymmetr Catalysis & Synth, CH-1015 Lausanne, Switzerland
基金
欧盟地平线“2020”;
关键词
NATURAL-PRODUCTS; OPTICALLY PURE; MOLECULAR-REARRANGEMENTS; CYCLOADDITION REACTIONS; TARTARIC-ACIDS; NEF REACTION; RING-SYSTEM; EQUIVALENTS; DERIVATIVES; PLATENSIMYCIN;
D O I
10.1071/CH16428
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Diels-Alder reaction is one of the most powerful, well-established, and versatile reactions in organic chemistry; however, its application in certain settings remains a challenge as a result of functional group incompatibility. In this review, we examine the methods in which masked ketenes can be employed as dienophiles, taking particular note of applications in complex settings.
引用
收藏
页码:1365 / 1374
页数:10
相关论文
共 50 条
  • [21] Diels-Alder Reaction of Polychlorocyclopentadienes with Vinyl-and Allylacetylene Dienophiles
    M. G. Veliev
    A. Z. Chalabieva
    M. I. Shatirova
    I. M. Mamedov
    E. Sh. Mamedov
    Russian Journal of Organic Chemistry, 2004, 40 : 946 - 952
  • [22] OXAZOLES AS DIENOPHILES IN DIELS-ALDER REACTIONS
    DONDONI, A
    FOGAGNOLO, M
    MASTELLARI, A
    PEDRINI, P
    UGOZZOLI, F
    TETRAHEDRON LETTERS, 1986, 27 (33) : 3915 - 3918
  • [23] Diels-Alder reaction of 4-halogenated masked o-benzoquinones with electron-rich dienophiles
    Surasani, Seshi Reddy
    Peddinti, Rama Krishna
    TETRAHEDRON LETTERS, 2011, 52 (36) : 4615 - 4618
  • [24] Furans act as dienophiles in facile Diels-Alder reactions with masked o-benzoquinones
    Chen, CH
    Rao, PD
    Liao, CC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (50) : 13254 - 13255
  • [25] SOME NEW DIENOPHILES IN THE DIELS-ALDER REACTION WITH ACTIVE CYCLIC DIENES
    VELIEV, MG
    GUSEINOV, MM
    YANOVSKAYA, LA
    BURSTEIN, KY
    TETRAHEDRON, 1985, 41 (04) : 749 - 761
  • [26] Diels-Alder reaction of deactivated dienes with electron-poor dienophiles
    Chattopadhyay, S
    Mahadani, D
    Acharya, DP
    Ghoshal, N
    Achari, B
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1996, 35 (06): : 605 - 607
  • [27] Cationic iron aminocarbene complexes as dienophiles in Diels-Alder reaction with cyclopentadiene
    RuckBraun, K
    Kuhn, J
    CHEMISCHE BERICHTE, 1996, 129 (09) : 1057 - 1059
  • [28] Reactivity and stereoselectivity of the Diels-Alder reaction using cyclic dienophiles and siloxyaminobutadienes
    Ohfusa, Toshiyuki
    Nishida, Atsushi
    TETRAHEDRON, 2011, 67 (10) : 1893 - 1906
  • [29] Strained allenes as dienophiles in the Diels-Alder reaction: An experimental and computational study
    Nendel, M
    Tolbert, LM
    Herring, LE
    Islam, MN
    Houk, KN
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03): : 976 - 983
  • [30] ELECTRON-TRANSFER INITIATED DIELS-ALDER REACTION WITH ALLENES AS DIENOPHILES
    SCHMITTEL, M
    WOHRLE, C
    TETRAHEDRON LETTERS, 1993, 34 (52) : 8431 - 8434