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
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
  • [41] Highly efficient ring opening reactions of epoxides with deactivated aromatic amines catalyzed by heteropoly acids in water
    Azizi, Najmedin
    Saidi, Mohammad R.
    TETRAHEDRON, 2007, 63 (04) : 888 - 891
  • [42] Visible-Light-Mediated Ring-Opening Reactions of Cyclopropanes
    Sivanandan, Sudheesh T.
    Bharath Krishna, R.
    Baiju, Thekke V.
    Mohan, Chithra
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (48) : 6781 - 6805
  • [43] Graphite oxide: a simple and efficient solid acid catalyst for the ring-opening of epoxides by alcohols
    Mirza-Aghayan, Maryam
    Alizadeh, Mahdi
    Tavana, Mahdieh Molaee
    Boukherroub, Rabah
    TETRAHEDRON LETTERS, 2014, 55 (49) : 6694 - 6697
  • [44] Ring-opening and ring-expansion reactions of carborane-fused borirane
    Wang, Hanqiang
    Zhang, Jie
    Xie, Zuowei
    CHEMICAL SCIENCE, 2021, 12 (39) : 13187 - 13192
  • [45] Catalysis of 1,1,3,3-tetrafluorohexylethyldistannoxane in the ring-opening reaction of epoxides
    Xiang, JN
    Yin, X
    Chen, CY
    Fan, HL
    He, CL
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2004, 25 (09): : 1662 - 1665
  • [46] Efficient synthesis of chlorohydrins: ionic liquid promoted ring-opening reaction of epoxides and TMSCl
    Xu, LW
    Li, L
    Xia, CG
    Zhao, PQ
    TETRAHEDRON LETTERS, 2004, 45 (11) : 2435 - 2438
  • [47] Quaternary ammoniums and a cationic sodium complex as supramolecular catalysts in ring-opening of epoxides by amines
    Thomas, Coralie
    Brut, Sebastien
    Bibal, Brigitte
    TETRAHEDRON, 2014, 70 (08) : 1646 - 1650
  • [49] Research Progress in the Ring-Opening Reactions of Aziridines by Carbon Nucleophiles
    Chu, Xu
    Chang, Honghong
    Gao, Wenchao
    Wei, Wenlong
    Li, Xing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (10) : 2569 - 2589
  • [50] Stereoselective Synthesis of Contiguous Cyclopropylaziridines: Enabling the Construction of Versatile Chiral Molecules Including γ-Lactams via Ring-Opening Reactions
    Han, Jiho
    Ha, Hyun-Joon
    Yang, Jung Woon
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (12) : 1970 - 1976