Recent advances in the controlled preparation of poly(α-hydroxy acids):: Metal-free catalysts and new monomers

被引:148
作者
Bourissou, Didier [1 ]
Moebs-Sanchez, Sylvie [1 ]
Martin-Vaca, Blance [1 ]
机构
[1] Univ Toulouse 3, CNRS, UMR 5069, Lab Heterochim Fondamentale & Appl, F-31062 Toulouse 09, France
关键词
a-hydroxy acids; organocatalysis; enzymatic catalysis; 1,4-Dioxane-2,5-diones; O-Carboxy anhydrides;
D O I
10.1016/j.crci.2007.05.004
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Polylactides (PLAs) are at the forefront of biodegradable polymer research. These poly(alpha-hydroxy acids) can be prepared by polycondensation of lactic acid or ring-opening polymerization (ROP) of lactide, both routes typically involving metallic promoters. The first part of this review focuses on the recent achievements reported with metal-free systems via organocatalytic (nucleophilic, cationic and bifunctional) as well as enzymatic approaches. The second part of the review concerns the heterocyclic monomers that give access to poly(alpha-hydroxy acids) such as PLAs. Two complementary approaches will be discussed: substituted 1,4-dioxane-2,5-diones and synthetic equivalents thereof. To cite this article: D. Bourissou et al., C. R. Chimie 10 (2007). (c) 2007 Academie, des sciences. Published by Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:775 / 794
页数:20
相关论文
共 119 条
  • [1] ABAYASINGHE N, 2000, POLYM PREPR AM CHEM, V42, P485
  • [2] Synthesis of poly(lactic acid) by direct polycondensation of lactic acid using 1,1′-carbonyldiimidazole, N,N,N′,N′-tetramethylchloroformamidinium chloride, and N,N′-dicyclohexylcarbodiimide as condensing agents
    Akutsu, F
    Inoki, M
    Uei, H
    Sueyoshi, M
    Kasashima, Y
    Naruchi, K
    Yamaguchi, Y
    Sunahara, M
    [J]. POLYMER JOURNAL, 1998, 30 (05) : 421 - 423
  • [3] Looking for stable carbenes: The difficulty in starting anew
    Arduengo, AJ
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (11) : 913 - 921
  • [4] Cationic copolymerization of ε-caprolactone and L,L-lactide by an activated monomer mechanism
    Basko, Maigorzata
    Kubisa, Przemysiaw
    [J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2006, 44 (24) : 7071 - 7081
  • [5] BEN F, 2005, Patent No. 20051004391
  • [6] Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts
    Berkessel, A
    Cleemann, F
    Mukherjee, S
    Müller, TN
    Lex, J
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (05) : 807 - 811
  • [7] Second-generation organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones
    Berkessel, A
    Mukherjee, S
    Cleemann, F
    Müller, TN
    Lex, J
    [J]. CHEMICAL COMMUNICATIONS, 2005, (14) : 1898 - 1900
  • [8] Stable carbenes
    Bourissou, D
    Guerret, O
    Gabbaï, FP
    Bertrand, G
    [J]. CHEMICAL REVIEWS, 2000, 100 (01) : 39 - 91
  • [9] Controlled cationic polymerization of lactide
    Bourissou, D
    Martin-Vaca, B
    Dumitrescu, A
    Graullier, M
    Lacombe, F
    [J]. MACROMOLECULES, 2005, 38 (24) : 9993 - 9998
  • [10] BOURISSOU D, 2006, Patent No. 06037812