Efficient Horner-Wadsworth-Emmons intramolecular cyclisation of a N-substituted phthalimide promoted by KF-Alumina: a general tool for the synthesis of functionalised isoindolinones

被引：34
作者：
Pace, Vittorio [1 ]
Martinez, Fernando [1 ]
Nova, Clara I. [2 ]
Fernandez, Maria [1 ]
Vicente Sinisterra, Jose [1 ,2 ]
Alcantara, Andres R. [1 ,2 ]
机构：
[1] Univ Complutense, Dept Organ & Pharmaceut Chem, Fac Pharm, E-28040 Madrid, Spain
[2] SBI, Madrid, Spain
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 25期
关键词：
Horner-Wadsworth-Emmons reaction; Isoindolinones; Cyclisation; Heterogeneous catalysis; Enones; ORGANIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; DIASTEREOSELECTIVE ROUTE; SUPPORTED REAGENTS; DERIVATIVES; ISOINDOLIN-1-ONES; CONDENSATION; WITTIG; PHTHALALDEHYDE; REARRANGEMENT;
D O I：
10.1016/j.tetlet.2009.04.029
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An intramolecular Horner-Wadsworth-Emmons reaction promoted by KF-Alumina involving a N-substituted phthalimide, cleanly and efficiently furnishes an interesting alpha,beta-unsaturated tricyclic enone which may undergo selective alkylations at the alpha'-position. (C) 2009 Elsevier Ltd. All rights reserved.
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收藏
页码：3050 / 3053
页数：4
相关论文
共 53 条
  • [1] Flash vacuum pyrolysis of stabilised phosphorus ylides .7. Cyclisation of amino acid derived alpha-phthalimidoacyl ylides to give pyrroloisoindolediones
    Aitken, RA
    Cooper, HR
    Mehrotra, AP
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (05): : 475 - 483
  • [2] Recent advances in KF/alumina promoted organic reactions
    Basu, Basudeb
    Das, Pralay
    Das, Sajal
    [J]. CURRENT ORGANIC CHEMISTRY, 2008, 12 (02) : 141 - 158
  • [3] SYNTHESIS OF PYRROLIZIDINEDIONES FROM CYCLIC N,N-DIACYLAMINO ACIDS
    BESTMANN, HJ
    MOENIUS, T
    SOLIMAN, F
    [J]. CHEMISTRY LETTERS, 1986, (09) : 1527 - 1528
  • [4] THE MICHAELIS-ARBUZOV REARRANGEMENT
    BHATTACHARYA, AK
    THYAGARAJAN, G
    [J]. CHEMICAL REVIEWS, 1981, 81 (04) : 415 - 430
  • [5] KF/Al2O3 mediated organic synthesis
    Blass, BE
    [J]. TETRAHEDRON, 2002, 58 (46) : 9301 - 9320
  • [6] BOULLET FM, 1985, TETRAHEDRON, V41, P1259
  • [7] REDUCTION OF PHTHALIC ACID AND ITS DERIVATIVES BY ZINC
    BREWSTER, JH
    FUSCO, AM
    CORMAN, BG
    CAROSINO, LE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (02) : 498 - &
  • [8] 1-Phthalimido-4-(3-indolyl)-2-siloxy-1,3-butadienes:: synthesis and Diels-Alder reactivity
    Caballero, E
    Alonso, D
    Peláez, R
    Alvarez, C
    Puebla, P
    Sanz, F
    Medarde, M
    Tomé, F
    [J]. TETRAHEDRON LETTERS, 2004, 45 (08) : 1631 - 1634
  • [9] MECHANISM OF REACTION BETWEEN TRIALKYL PHOSPHITES AND ALPHA-HALOGENATED KETONES
    CHOPARD, PA
    CLARK, VM
    HUDSON, RF
    KIRBY, AJ
    [J]. TETRAHEDRON, 1965, 21 (08) : 1961 - &
  • [10] LDA-induced metalation of isoindolinones. An efficient route to 3-substituted isoindoline derivatives
    Couture, A
    Deniau, E
    Ionescu, D
    Grandclaudon, P
    [J]. TETRAHEDRON LETTERS, 1998, 39 (16) : 2319 - 2320
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