Oxazolines as chiral building blocks for imidazolium salts and N-heterocyclic carbene ligands

被引:235
|
作者
Glorius, F [1 ]
Altenhoff, G [1 ]
Goddard, R [1 ]
Lehmann, C [1 ]
机构
[1] Max Planck Inst Kohlenforsch, Kaiser Wilhelm Pl 1, D-45470 Mulheim, Germany
关键词
D O I
10.1039/b208045a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enantiomerically pure imidazolium triflates can be readily prepared from bioxazolines and oxazolineimines; deprotonation of imidazolium triflate 2 gives a chiral N-heterocyclic carbene that can act as a ligand in a catalytically active palladium complex.
引用
收藏
页码:2704 / +
页数:2
相关论文
共 50 条
  • [1] Development of building blocks for the synthesis of N-heterocyclic carbene ligands
    Xu, GP
    Gilbertson, SR
    ORGANIC LETTERS, 2005, 7 (21) : 4605 - 4608
  • [2] Chiral bicyclic imidazolium salts as a new class of N-heterocyclic carbene precursors
    Matsuoka, Yuki
    Ishida, Yasuhiro
    Saigo, Kazuhiko
    TETRAHEDRON LETTERS, 2008, 49 (18) : 2985 - 2989
  • [3] From Imidazole toward Imidazolium Salts and N-Heterocyclic Carbene Ligands: Electronic and Geometrical Redistribution
    Velle, Alba
    Cebollada, Andrea
    Macias, Ramon
    Gil-Moles, Maria
    Miguel, Pablo J. Sanz
    ACS OMEGA, 2017, 2 (04): : 1392 - 1399
  • [4] Synthesis of N-heterocyclic carbene building blocks and their applications
    Zhao, Yang
    Gilbertson, Scott R.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [5] Imidazolium salicylaldimine frameworks for the preparation of tridentate N-heterocyclic carbene ligands
    Ulusoy, Mahmut
    Sahin, Onur
    Bueyuekguengoer, Orhan
    Cetinkaya, Bekir
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (10) : 1895 - 1902
  • [6] Chiral N-heterocyclic carbene ligands based on a biisoquinoline template
    Cavell, Kingsley J.
    Elliott, Mark C.
    Nielsen, David J.
    Paine, James S.
    DALTON TRANSACTIONS, 2006, (41) : 4922 - 4925
  • [7] Hybrid ligands with N-heterocyclic carbene and chiral phosphaferrocene components
    Willms, Holger
    Frank, Walter
    Ganter, Christian
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (09) : 2719 - 2729
  • [8] N-Heterocyclic carbenes: VI. Abietane-based chiral benzimidazolium salts as N-heterocyclic carbene ligands in the heck reaction
    Glushkov, V. A.
    Teplykh, E. N.
    Denisov, M. S.
    Gorbunov, A. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 48 (06) : 815 - 819
  • [9] N-Heterocyclic carbenes: VI. Abietane-based chiral benzimidazolium salts as N-heterocyclic carbene ligands in the heck reaction
    V. A. Glushkov
    E. N. Teplykh
    M. S. Denisov
    A. A. Gorbunov
    Russian Journal of Organic Chemistry, 2012, 48 : 815 - 819
  • [10] N-Heterocyclic Carbene Ligands Having Planar Chiral Ferrocene Structure
    Yoshida, Kazuhiro
    Yasue, Risa
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2020, 78 (01) : 32 - 44