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
  • [41] Formation of N-sulfonylcarbamates from epichlorohydrin:: Synthesis of polyfunctional oxazolidin-2-ones
    Rmedi, Hamdi
    Beji, Mohamed
    Baklouti, Ahmed
    SYNTHETIC COMMUNICATIONS, 2007, 37 (13) : 2215 - 2223
  • [42] Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water
    Buyck, Thomas
    Pasche, Delphine
    Wang, Qian
    Zhu, Jieping
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (07) : 2278 - 2281
  • [43] Parallel Kinetic Resolution of D-Labelled 2-Aryl-Propionic and Butanoic Acids Using Quasi-Enantiomeric Combinations of Oxazolidin-2-Ones
    Coulbeck, Elliot
    Dingjan, Marco
    Eames, Jason
    CHIRALITY, 2010, 22 (02) : 193 - 205
  • [44] D-xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective aldol reactions
    Lutzen, A
    Koll, P
    TETRAHEDRON-ASYMMETRY, 1997, 8 (08) : 1193 - 1206
  • [45] One-pot conversion of alkenes into oxazolines and oxazolidin-2-ones promoted by diphenyl diselenide
    Tiecco, M
    Testaferri, L
    Marini, F
    Temperini, A
    Bagnoli, L
    Santi, C
    SYNTHETIC COMMUNICATIONS, 1997, 27 (23) : 4131 - 4140
  • [46] An improved procedure for the palladium-catalyzed oxidative carbonylation of β-amino alcohols to oxazolidin-2-ones
    Gabriele, B
    Mancuso, R
    Salerno, G
    Costa, M
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02): : 601 - 604
  • [47] Polymer supported oxazolidin-2-ones derived from L-serine - a cautionary tale
    Bew, SP
    Bull, SD
    Davies, SG
    TETRAHEDRON LETTERS, 2000, 41 (39) : 7577 - 7581
  • [48] D-Xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective acylations and halogenations
    Lutzen, A
    Koll, P
    TETRAHEDRON-ASYMMETRY, 1997, 8 (01) : 29 - 32
  • [49] Regio- and stereoselective synthesis of functionalized oxazolidin-2-ones from the reaction of α-epoxyketones with urea
    Nikpour, Farzad
    Mohebbi, Sajjad
    Paibast, Touraj
    Beigvand, Mahdi
    MONATSHEFTE FUR CHEMIE, 2008, 139 (06): : 663 - 667
  • [50] D-Xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective acylations and halogenations
    Luetzen, A.
    Koell, P.
    Tetrahedron: Asymmetry, 8 (01):