Tools for studying aqueous enantioselective lanthanide-catalyzed Mukaiyama aldol reactions

被引:15
作者
Averill, Derek J. [1 ]
Allen, Matthew J. [1 ]
机构
[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
基金
美国国家科学基金会;
关键词
LEWIS-ACID CATALYSTS; SILYL ENOL ETHERS; LUMINESCENCE-DECAY; SPECTROSCOPIC CHARACTERIZATION; EUROPIUM(III) IONS; WATER-MOLECULES; MEDIA; COMPLEXES; LIGANDS; YTTERBIUM;
D O I
10.1039/c4cy01117a
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Enantioselective bond-forming reactions catalyzed by chiral lanthanide-based complexes are popular because of their Lewis acidity, solvent compatibility, reusability, and potential to catalyze reactions with high stereospecificity. The stereospecific outcomes of bond-forming reactions catalyzed by asymmetric lanthanide-based precatalysts depend on the coordination chemistry of the precatalysts that can be interrogated with X-ray crystal structures, luminescence measurements, NMR spectroscopy, and computational methods. This review is primarily focused on developments related to lanthanide-based precatalysts since the turn of the century and the techniques used to study coordination environments of lanthanide-based precatalysts for Mukaiyama aldol reactions in aqueous media.
引用
收藏
页码:4129 / 4137
页数:9
相关论文
共 56 条
  • [1] Solution Chemistry of Europium(III) Aqua Ion at Micromolar Concentrations as Probed by Direct Excitation Luminescence Spectroscopy
    Andolina, Christopher M.
    Mathews, Ryan A.
    Morrow, Janet R.
    [J]. HELVETICA CHIMICA ACTA, 2009, 92 (11) : 2330 - 2348
  • [2] Synthesis, Spectroscopic Characterization, and Reactivity of Water-Tolerant Eu3+-Based Precatalysts
    Averill, Derek J.
    Allen, Matthew J.
    [J]. INORGANIC CHEMISTRY, 2014, 53 (12) : 6257 - 6263
  • [3] The Role of Water in Lanthanide-Catalyzed Carbon-Carbon Bond Formation
    Averill, Derek J.
    Dissanayake, Prabani
    Allen, Matthew J.
    [J]. MOLECULES, 2012, 17 (02) : 2073 - 2081
  • [4] Non-radiative deactivation of the excited states of europium, terbium and ytterbium complexes by proximate energy-matched OH, NH and CH oscillators: an improved luminescence method for establishing solution hydration states
    Beeby, A
    Clarkson, IM
    Dickins, RS
    Faulkner, S
    Parker, D
    Royle, L
    de Sousa, AS
    Williams, JAG
    Woods, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (03): : 493 - 503
  • [5] Steady-state luminescence investigation of the binding of Eu(III) and Tb(III) ions with synthetic peptides derived from plant thionins
    Bemquerer, MP
    Bloch, C
    Brito, HF
    Teotonio, EES
    Miranda, MTM
    [J]. JOURNAL OF INORGANIC BIOCHEMISTRY, 2002, 91 (02) : 363 - 370
  • [6] ENANTIOMERIC RECOGNITION OF ORGANIC AMMONIUM-SALTS BY CHIRAL DIALKYL-SUBSTITUTED, DIALKENYL-SUBSTITUTED, AND TETRAMETHYL-SUBSTITUTED PYRIDINO-18-CROWN-6 AND TETRAMETHYL-SUBSTITUTED BIS-PYRIDINO-18-CROWN-6 LIGANDS - COMPARISON OF TEMPERATURE-DEPENDENT H-1-NMR AND EMPIRICAL FORCE-FIELD TECHNIQUES
    BRADSHAW, JS
    HUSZTHY, P
    MCDANIEL, CW
    ZHU, CY
    DALLEY, NK
    IZATT, RM
    LIFSON, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) : 3129 - 3137
  • [7] Taking advantage of luminescent lanthanide ions
    Bünzli, JCG
    Piguet, C
    [J]. CHEMICAL SOCIETY REVIEWS, 2005, 34 (12) : 1048 - 1077
  • [8] Isoquinoline-Based Lanthanide Complexes: Bright NIR Optical Probes and Efficient MRI Agents
    Caille, Fabien
    Bonnet, Celia S.
    Buron, Frederic
    Villette, Sandrine
    Helm, Lothar
    Petoud, Stephane
    Suzenet, Franck
    Toth, Eva
    [J]. INORGANIC CHEMISTRY, 2012, 51 (04) : 2522 - 2532
  • [9] Correlation between ligand coordination number and the shift of the F-7(0)-5D(0) transition frequency in Europium(III) complexes
    Choppin, GR
    Wang, ZM
    [J]. INORGANIC CHEMISTRY, 1997, 36 (02) : 249 - 252
  • [10] (Tetracycline)europium(III) Complex as Luminescent Probe for Hydrogen Peroxide Detection
    Dehaen, Geert
    Absillis, Gregory
    Driesen, Kris
    Binnemans, Koen
    Parac-Vogt, Tatjana N.
    [J]. HELVETICA CHIMICA ACTA, 2009, 92 (11) : 2387 - 2397