EFFICIENT CLAISEN-TYPE CONDENSATION BETWEEN ACYL UNITS BOUND TO A MOLECULAR TEMPLATE

被引:16
|
作者
SUN, SG [1 ]
HARRISON, P [1 ]
机构
[1] MCMASTER UNIV,DEPT CHEM,1280 MAIN ST W,HAMILTON L8S 4M1,ONTARIO,CANADA
关键词
D O I
10.1016/0040-4039(93)88025-E
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Acylation of 3,4,7,8-tetramethylglycoluril1 (1) provides the monoacyl derivative 3 which can be acylated further with LDA and acyl chlorides. The resulting symmetric or asymmetric diacyl derivatives 4 undergo efficient base-catalyzed acyl transfer to provide 2-(acylacyl)glycolurils 5,6. Thus, 1 acts as a template to allow facile condensations between acyl units.
引用
收藏
页码:7715 / 7718
页数:4
相关论文
共 10 条
  • [1] Claisen-type condensation of vinylogous acyl triflates
    Kamijo, S
    Dudley, GB
    ORGANIC LETTERS, 2006, 8 (01) : 175 - 177
  • [2] Glycoluril as an efficient molecular template for intramolecular Claisen-type condensations
    Sun, SG
    Edwards, L
    Harrison, P
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (03): : 437 - 448
  • [4] Reductive Claisen-type condensation promoted by the combination of phosphine and Lewis acid
    Hashimoto, Y
    Konishi, H
    Kikuchi, S
    SYNLETT, 2004, (07) : 1264 - 1266
  • [5] 3-Keto-5-aminohexanoate Cleavage Enzyme A COMMON FOLD FOR AN UNCOMMON CLAISEN-TYPE CONDENSATION
    Bellinzoni, Marco
    Bastard, Karine
    Perret, Alain
    Zaparucha, Anne
    Perchat, Nadia
    Vergne, Carine
    Wagner, Tristan
    de Melo-Minardi, Raquel C.
    Artiguenave, Francois
    Cohen, Georges N.
    Weissenbach, Jean
    Salanoubat, Marcel
    Alzari, Pedro M.
    JOURNAL OF BIOLOGICAL CHEMISTRY, 2011, 286 (31) : 27399 - 27405
  • [6] Biomimetic decarboxylative condensation between malonate and acetate units attached to a glycoluril template
    Chen, H
    Harrison, PHM
    CANADIAN JOURNAL OF CHEMISTRY, 2002, 80 (06) : 601 - 607
  • [7] Molecular Bose-Einstein condensation and bound states in lithium niobate type ferroelectrics
    Biswas, A.
    Song, Y. M.
    JOURNAL OF OPTOELECTRONICS AND ADVANCED MATERIALS, 2015, 17 (11-12): : 1885 - 1890
  • [8] Langmuir-Blodgett Monolayer as an Efficient p-Conducting Channel of Ambipolar Organic Transistors and a Template for n-Type Molecular Alignment
    Wei, Zhongming
    Xu, Wei
    Hu, Wenping
    Zhu, Daoben
    LANGMUIR, 2009, 25 (06) : 3349 - 3351
  • [9] Lewis acid-containing mesoporous molecular sieves as solid efficient catalysts for solvent-free Mukaiyama-type aldol condensation
    Garro, R
    Navarro, MT
    Primo, J
    Corma, A
    JOURNAL OF CATALYSIS, 2005, 233 (02) : 342 - 350
  • [10] Distribution of dendritic, terminal and linear units and relationship between degree of branching and molecular weight of AB2-type hyperbranched polymer:: A 13C-NMR study
    Shanmugam, T.
    Raghavan, A.
    Nasar, A. Sultan
    JOURNAL OF MACROMOLECULAR SCIENCE PART A-PURE AND APPLIED CHEMISTRY, 2006, 43 (09): : 1387 - 1397