Stereoselective Ring-Opening Reactions of Epoxides in Water

被引：21
|
作者：
Bonollo, S. [1 ]
Lanari, D. [1 ]
Marrocchi, A. [1 ]
Vaccaro, L. [1 ]
机构：
[1] Univ Perugia, Lab Green Synthet Organ Chem, CEMIN, Dipartimento Chim, I-06123 Perugia, Italy
来源：
CURRENT ORGANIC SYNTHESIS | 2011年 / 8卷 / 03期
关键词：
Epoxide; water; stereoselective transformations; catalysis; HYDROLYTIC KINETIC RESOLUTION; ASYMMETRIC ALDOL REACTIONS; ORGANIC-REACTIONS; MESO-EPOXIDES; ALPHA; BETA-EPOXYCARBOXYLIC ACIDS; SODIUM-BOROHYDRIDE; SYNTHETIC APPLICATIONS; DIRECTED EVOLUTION; EFFICIENT CATALYST; AROMATIC-AMINES;
D O I：
10.2174/157017911795529191
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Water has proved to be an excellent reaction medium for the definition of highly chemically-efficient and environmentally-friendly synthetic processes. In several cases, by exploiting the unique properties of water it has been possible to realize more selective and efficient processes than those performed in organic media, including the ring-opening of epoxides by nucleophiles. In this review article the role of water in influencing the stereoselectivity of epoxide ring-opening reactions will be presented, including the most recent examples of enzyme-catalyzed processes.
引用
收藏
页码：319 / 329
页数：11
相关论文
共 50 条
  • [1] Ring-Opening of Epoxides in Water
    Bonollo, Simona
    Lanari, Daniela
    Vaccaro, Luigi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (14) : 2587 - 2598
  • [2] Asymmetric Ring-Opening of Epoxides Catalyzed by Metal-Salen Complexes
    Lidskog, Anna
    Li, Yutang
    Warnmark, Kenneth
    CATALYSTS, 2020, 10 (06)
  • [3] Ring Opening Reactions of Epoxides. A Review
    Thirumalaikumar, Muniappan
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2022, 54 (01) : 1 - 39
  • [4] Metal-Free Ring-Opening of Epoxides
    Kumar, Vikas
    Chimni, Swapandeep Singh
    CHEMISTRYSELECT, 2023, 8 (35):
  • [5] Regio- and Stereoselective Ring Opening of Allylic Epoxides
    Pineschi, Mauro
    Bertolini, Ferruccio
    Di Bussolo, Valeria
    Crotti, Paolo
    CURRENT ORGANIC SYNTHESIS, 2009, 6 (03) : 290 - 324
  • [6] Asymmetric Ring-Opening Reactions of meso-Epoxides Using Metal-Chiral Bipyridine Complexes
    Ogawa, Chikako
    Kokubo, Masaya
    Kobayashi, Shu
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2010, 68 (07) : 718 - 728
  • [7] InCl3-catalyzed regioselective ring-opening reactions of epoxides to β-hydroxy ethers
    Kim, BH
    Piao, FY
    Lee, EJ
    Kim, JS
    Jun, YM
    Lee, BM
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2004, 25 (06) : 881 - 888
  • [8] Progress in Transition Metal-Catalyzed Asymmetric Ring-Opening Reactions of Epoxides and Aziridines
    Du Qingfeng
    Zhang Lu
    Gao Feng
    Wang Le
    Zhang Wanbin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (10) : 3240 - 3262
  • [9] Catalytic Performance of [Fe] for Regioselective Ring-opening of Epoxides
    Yao Yixuan
    Lu Changbo
    Zhang Hongwei
    Zhang Duxin
    Shang Hongyan
    Tian Yuanyu
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2023, 44 (08):
  • [10] Scandium-catalyzed ring-opening desymmetrization of meso-epoxides
    Ogawa, Chikako
    Wang, Naiwei
    Boudou, Marine
    Azoulay, Stephane
    Manabe, Kei
    Kobayashi, Shu
    HETEROCYCLES, 2007, 72 : 589 - 598
12345