Resolution of pentafluorophenyl esters using oxazolidin-2-ones

被引:0
|
作者
Al Shaye, Najla [1 ]
Eames, Jason [1 ]
机构
[1] Univ Hull, Dept Chem, Kingston Upon Hull HU6 7RX, Yorks, England
关键词
PARALLEL KINETIC RESOLUTION; ENANTIOMERIC EVANS OXAZOLIDINONES; ACIDS; COMBINATION; AUXILIARY; ALKYLATION; PROFENS;
D O I
10.1016/j.tetlet.2010.08.109
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of structurally related racemic pentafluorophenyl active esters were resolved using an equimolar amount of (S)-4-phenyloxazolidin-2-one. The levels of diastereocontrol were found to be excellent (80-96% de) at similar to 40% conversion. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5892 / 5895
页数:4
相关论文
共 50 条
  • [31] Resolution of active esters using Oxazolidin-2-thione
    AlShaye, Najla A.
    Eames, Jason
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [32] Reaction of 2-{[2-(ethenyloxy)ethoxy]methyl}oxirane with oxazolidin-2-ones
    N. A. Lobanova
    E. Kh. Sadykov
    V. K. Stankevich
    Russian Journal of Organic Chemistry, 2016, 52 : 553 - 557
  • [33] Reaction of 2-{[2-(ethenyloxy)ethoxy]methyl}oxirane with oxazolidin-2-ones
    Lobanova, N. A.
    Sadykov, E. Kh.
    Stankevich, V. K.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (04) : 553 - 557
  • [34] Synthesis of aryloxy(alcoxy)sulfonyl-5-F-hexyl oxazolidin-2-ones
    Rmedi, H.
    Beji, M.
    Baklouti, A.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (02) : 349 - 356
  • [35] ON THE MECHANISM OF PD(O) CATALYZED FORMATION OF OXAZOLIDIN-2-ONES FROM VINYL EPOXIDES
    TROST, BM
    HURNAUS, R
    TETRAHEDRON LETTERS, 1989, 30 (30) : 3893 - 3896
  • [36] Rearrangements and racemisation during the synthesis of L-serine derived oxazolidin-2-ones
    Bew, SP
    Bull, SD
    Davies, SG
    Savory, ED
    Watkin, DJ
    TETRAHEDRON, 2002, 58 (46) : 9387 - 9401
  • [37] D-xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective alkylations
    Koll, P
    Lutzen, A
    TETRAHEDRON-ASYMMETRY, 1996, 7 (03) : 637 - 640
  • [38] Electrogenerated base-induced N-acylation of chiral oxazolidin-2-ones
    Feroci, M
    Inesi, A
    Palombi, L
    Rossi, L
    Sotgiu, G
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (18): : 6185 - 6188
  • [39] An efficient asymmetric desymmetrization of prochiral glutaric anhydrides with SuperQuat chiral oxazolidin-2-ones
    Chaubey, Narendra
    Date, Sonali M.
    Ghosh, Sunil K.
    TETRAHEDRON-ASYMMETRY, 2008, 19 (23) : 2721 - 2730
  • [40] Ruthenium Porphyrin Catalyzed Synthesis of Oxazolidin-2-ones by Cycloaddition of CO2 to Aziridines
    Carminati, Daniela
    Gallo, Emma
    Damiano, Caterina
    Caselli, Alessandro
    Intrieri, Daniela
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2018, (48) : 5258 - 5262