(±)-1,1′-Binaphthalene-2,2′-diol-derived phosphoric diester: immobilization on polyethylene glycol support and application in the Pudovik reaction

被引:0
|
作者
I. P. Beletskaya
L. S. Patrikeeva
F. Lamaty
机构
[1] M. V. Lomonosov Moscow State University,Department of Chemistry
[2] Montpellier University 2,Max Mousseron Institute of Biomolecules (IBMM)
来源
Russian Chemical Bulletin | 2011年 / 60卷
关键词
(±)-BINOL; phosphoric acids; polyethylene glycol; α-aminophosphonates; the Pudovik reaction; recyclization;
D O I
暂无
中图分类号
学科分类号
摘要
(±)-1,1′-Binaphthalene-2,2′-diol (BINOL) was immobilized on polyethylene glycol (PEG) by means of triazole linkers, which were constructed by the [3+2] cycloaddition between azide and ethynyl fragments, preliminary incorporated into the molecules of these reactants. Treatment of these BINOL derivatives with phosphorus oxychloride leads to the corresponding PEG-immobilized 1,1′-binaphthalene-2,2′-diylphosphoric acids. The latter efficiently catalyze the Pudovik reaction and can be reused without loss of catalytic activity.
引用
收藏
页码:2370 / 2374
页数:4
相关论文
共 50 条
  • [41] Optically active aromatic polyimides having axially dissymmetric 1,1'-binaphthalene-2,2'-diyl units
    Mi, QD
    Gao, LX
    Ding, MX
    MACROMOLECULES, 1996, 29 (17) : 5758 - 5759
  • [42] A new convenient method for the resolution of 1,1′-binaphthalene-2, 2′-diol via a phosphite using (-)-menthol as resolving agent
    Cai, JX
    Zhou, ZH
    Li, KY
    Yeung, CH
    Tang, CC
    CHINESE CHEMICAL LETTERS, 2002, 13 (07) : 617 - 619
  • [43] Preparation of Molecularly Imprinted Polymer for Chiral Recognition of Racemic 1,1′-Binaphthalene-2,2′-Diamine by HPLC
    Dong, H.
    Wang, Y.
    Ou, Y.
    She, J.
    Shen, X.
    Li, J.
    Zhang, C.
    Liu, L.
    ACTA CHROMATOGRAPHICA, 2014, 26 (04) : 683 - 693
  • [44] ASYMMETRIC [2+2] CYCLOADDITION OF KETENE WITH ALDEHYDES CATALYZED BY ME3AL COMPLEXES OF AXIALLY CHIRAL 1,1'-BINAPHTHALENE-2,2'-DIOL DERIVATIVES
    TAMAI, Y
    SOMEYA, M
    FUKUMOTO, J
    MIYANO, S
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (12): : 1549 - 1550
  • [45] The Crystal Structure of a Benzyltriethylammonium Bromide Complex with rac-1,1′-Binaphthalene-2,2′-diol: The Inclusion of an Arylammonium Salt by an Assembly of Binaphthol Groups
    Marfo-Owusu, Emmanuel
    Thompson, Amber L.
    X-RAY STRUCTURE ANALYSIS ONLINE, 2021, 37 : 7 - 8
  • [46] New cholesteric comb-shaped polymers based on (S)-(+)-1,1′-binaphthalene-2,2′-diylphosphoric acid
    Kalinovskii, IO
    Boiko, NI
    Shibaev, PV
    Shibaev, VP
    VYSOKOMOLEKULYARNYE SOEDINENIYA SERIYA A & SERIYA B, 1998, 40 (03): : 389 - 396
  • [47] Chiral recognition and behavior of [1,1′-binaphthalene]-2,2′-diol in aqueous solution by fluorescence spectroscopy
    Xu, YF
    McCarroll, M
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2006, 178 (01) : 50 - 56
  • [48] Absolute Configuration of 3,3-Diphenyl-[2,2′-binaphthalene]-1,1′-diol Revisited
    Polavarapu, Prasad L.
    Petrovic, Ana G.
    Vick, Sarah E.
    Wulff, William D.
    Ren, Hong
    Ding, Zhensheng
    Staples, Richard J.
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15): : 5451 - 5457
  • [49] New cholesteric comb-shaped polymers based on (S)-(+)-1,1'-binaphthalene-2,2'-diylphosphoric acid
    Kalinovskij, I.O.
    Bojko, N.I.
    Shibaev, P.V.
    Shibaev, V.P.
    Vysokomolekularnye Soedineniya. Ser.A Ser.B Ser.C - Kratkie Soobshcheniya, 1998, 40 (01): : 389 - 396
  • [50] Electrochemical Synthesis of 1,1′-Binaphthalene-2,2′-Diamines via Transition-Metal-Free Oxidative Homocoupling
    Fan, Duona
    Khalid, Md. Imrul
    Kamble, Ganesh Tatya
    Sasai, Hiroaki
    Takizawa, Shinobu
    SUSTAINABLE CHEMISTRY, 2022, 3 (04): : 551 - 557