Synthesis and catalytic activity of the thermoresponsive polymers having pyrrolidine side chains as base functionalities

被引：0
|
作者：
机构：
[1] Uemukai, Toru
[2] Ishifune, Manabu
来源：
Ishifune, M. (ishifune@apch.kindai.ac.jp) | 1600年 / John Wiley and Sons Inc卷 / 129期
关键词：
Optically active polymers having chiral 2-aminomethylpyrrolidine side chains have been newly synthesized by a radical homopolymerization of the corresponding protected acrylamide monomer and copolymerization with N-isopropylacrylamide followed by deprotection. The resulting polymers were found to be thermoresponsive showing lower critical solution temperatures (LCSTs) at 27-65°C in their aqueous solutions. The pyrrolidine side chains of the resulting thermoresponsive polymer promoted aldol reaction between cyclohexanone and p-nitrobenzaldehyde in water; and the reaction proceeded most smoothly at its LCST. Moreover; the diastereomeric ratio (syn: anti) of the aldol adducts obtained at the reaction at 40°C was 22: 78; whereas the diastereomeric ratio (syn: anti) was 55: 45 at 20°C. These results indicate that the pyrrolidine side chains catalyze the aldol reactions in the relatively hydrophobic field generated by the thermoresponsive polymer at its LCST. Copyright © 2013 Wiley Periodicals; Inc;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Journal article (JA)
引用
收藏
相关论文
共 50 条
  • [41] Recent Advances in the Stereoselective Total Synthesis of Natural Pyranones Having Long Side Chains
    Avula, Satya Kumar
    Das, Biswanath
    Csuk, Rene
    Al-Rawahi, Ahmed
    Al-Harrasi, Ahmed
    MOLECULES, 2020, 25 (08):
  • [42] Synthesis of laminarin oligosaccharide derivatives having D-arabinofuranosyl side-chains
    He, HM
    Gu, GF
    Du, YG
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 2003, 22 (05) : 275 - 283
  • [43] Efficient catalytic synthesis of dendritic polymers having internal fluorescence labels for bioconjugation
    Chen, Guanghui
    Felgner, Philip L.
    Guan, Zhibin
    BIOMACROMOLECULES, 2008, 9 (07) : 1745 - 1754
  • [44] Novel fluorinated polymers bearing phosphonated side chains: synthesis, characterization and properties
    Zhu, Yuanqin
    Chen, Haihua
    He, Chuanglong
    JOURNAL OF POLYMER RESEARCH, 2011, 18 (06) : 1409 - 1416
  • [45] SYNTHESIS AND PROPERTIES OF ACRYLIC POLYMERS WITH OMEGA-FUNCTIONALIZED SIDE-CHAINS
    FISCHER, K
    EISENBACH, CD
    MAKROMOLEKULARE CHEMIE-RAPID COMMUNICATIONS, 1988, 9 (07): : 503 - 511
  • [46] Synthesis of porous polymers utilizing crystallization of hydrophobic long alkyl side chains
    Minamitani, K
    Gotoh, T
    Sakohara, S
    KOBUNSHI RONBUNSHU, 1998, 55 (03) : 137 - 144
  • [47] Novel fluorinated polymers bearing phosphonated side chains: synthesis, characterization and properties
    Yuanqin Zhu
    Haihua Chen
    Chuanglong He
    Journal of Polymer Research, 2011, 18 : 1409 - 1416
  • [48] Synthesis of iron-containing polymers with Azo dyes in the backbones or side chains
    Abd-El-Aziz, AS
    Okasha, RM
    Todd, EK
    Afifi, TH
    Shipman, PO
    Copping, KMD
    MACROMOLECULAR SYMPOSIA, 2004, 209 : 185 - 193
  • [49] ROLE OF HISTIDINE SIDE CHAINS IN CATALYTIC ACTIVITY OF B. CEREUS EXOPENICILLINASE
    FERENC, I
    MILE, I
    CSANYI, V
    ACTA BIOCHIMICA AND BIOPHYSICA ACADEMIAE SCIENTARIUM HUNGARICA, 1971, 6 (01): : 5 - &
  • [50] CATALYTIC ACTIVITY OF PARAMAGNETIC POLYMERS ON BASE OF ARYLDISULFIDES IN REACTION OF DIACETONE ALCOHOL
    PAUSHKIN, YM
    LOSEVA, LP
    DMITRIEV.LP
    LOSEV, YP
    ISAKOVIC.VI
    DOKLADY AKADEMII NAUK SSSR, 1973, 210 (04): : 865 - 868
12345