Polyfluoroarylation of oxazolones: access to non-natural fluorinated amino acids

被引：23
作者：
Teegardin, Kip A. [1 ]
Weaver, Jimmie D. [1 ]
机构：
[1] Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA
来源：
CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 35期
关键词：
F BOND ACTIVATION; C-F; PHOTOCATALYTIC HYDRODEFLUORINATION; FACILE ACCESS; FUNCTIONALIZATION; DERIVATIVES; OXAZOL-5-(4H)-ONES; AZLACTONES; INHIBITORS; ELECTRON;
D O I：
10.1039/c7cc01606a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Herein, conditions are provided for the formation and use of the oxazolone enolate for the nucleophilic substitution of highly fluorinated (hetero) arenes, which after unmasking yield highly fluorinated non-natural amino acids and derivatives. In addition, the properties and chemical behavior of this new class of amino acids are explored. The utility is demonstrated in the one pot synthesis of medicinally relevant 2-aminohydantoins.
引用
收藏
页码：4771 / 4774
页数：4
相关论文
共 25 条
  • [1] Functionalization of Fluorinated Molecules by Transition-Metal-Mediated C-F Bond Activation To Access Fluorinated Building Blocks
    Ahrens, Theresia
    Kohlmann, Johannes
    Ahrens, Mike
    Braun, Thomas
    [J]. CHEMICAL REVIEWS, 2015, 115 (02) : 931 - 972
  • [2] Asymmetric 1,4-Addition of Oxazolones to Nitroalkenes by Bifunctional Cinchona Alkaloid Thiourea Organocatalysts: Synthesis of α,α-Disubstituted α-Amino Acids
    Aleman, Jose
    Milelli, Andrea
    Cabrera, Silvia
    Reyes, Efraim
    Jorgensen, Karl Anker
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (35) : 10958 - 10966
  • [3] SCHIFF BASES .I. THERMAL DECARBOXYLATION OF ALPHA-AMINO-ACIDS IN PRESENCE OF KETONES
    ALSAYYAB, AF
    LAWSON, A
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (04): : 406 - &
  • [4] C-F Bond Activation in Organic Synthesis
    Amii, Hideki
    Uneyama, Kenji
    [J]. CHEMICAL REVIEWS, 2009, 109 (05) : 2119 - 2183
  • [5] Arylation of Azlactones using Diaryliodonium Bromides and Silver Carbonate: Facile Access to α-Tetrasubstituted Amino Acid Derivatives
    Chai, Zhuo
    Wang, Biao
    Chen, Jia-Nan
    Yang, Gaosheng
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (11-12) : 2714 - 2718
  • [6] 2D QSAR Studies on Series of Human Beta-secretase (BACE-1) Inhibitors
    Cruz, Daniela Santos
    Castilho, Marcelo Santos
    [J]. MEDICINAL CHEMISTRY, 2014, 10 (02) : 162 - 173
  • [7] 5-OXAZOLONES .2. 2,4-DIARYL-4-(2,4-DINITROARYL)-5(4H)-OXAZOLONES - SYNTHESIS AND ACID-CATALYZED TRANSFORMATION INTO 1-HYDROXY-1H-INDAZOLE-DERIVATIVES
    DANELLO, M
    ERBA, E
    GELMI, ML
    POCAR, D
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (01): : 67 - 73
  • [8] The diverse chemistry of oxazol-5-(4H)-ones
    Fisk, Jason S.
    Mosey, Robert A.
    Tepe, Jetze J.
    [J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (09) : 1432 - 1440
  • [9] Reactivity of Oxazol-5-(4H)-ones and Their Application toward Natural Product Synthesis
    Hewlett, N. M.
    Hupp, C. D.
    Tepe, J. J.
    [J]. SYNTHESIS-STUTTGART, 2009, (17): : 2825 - 2839
  • [10] Precious-Metal-Free Heteroarylation of Azlactones: Direct Synthesis of α-Pyridyl, α-Substituted Amino Acid Derivatives
    Johnson, Tarn C.
    Marsden, Stephen P.
    [J]. ORGANIC LETTERS, 2016, 18 (20) : 5364 - 5367
123