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
来源：
CATALYSIS SCIENCE & TECHNOLOGY | 2014年 / 4卷 / 12期
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 50 条
  • [21] Silver fluoride-catalyzed enantioselective Mukaiyama aldol additions to ketones
    Akullian, Laura C.
    Snapper, Marc L.
    Hoveyda, Amir H.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [22] Lanthanide-catalyzed endo- and enantioselective 1,3-dipolar cycloaddition reactions of nitrones with alkenes
    SanchezBlanco, AI
    Gothelf, KV
    Jorgensen, KA
    TETRAHEDRON LETTERS, 1997, 38 (45) : 7923 - 7926
  • [23] ENANTIOSELECTIVE AND DIASTEREOSELECTIVE CATALYSIS OF THE MUKAIYAMA ALDOL REACTION - ENE MECHANISM IN TITANIUM-CATALYZED ALDOL REACTIONS OF SILYL ENOL ETHERS
    MIKAMI, K
    MATSUKAWA, S
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) : 7039 - 7040
  • [24] Enantioselective Mukaiyama-aldol reaction of pyruvates and 1-phenyl-1-trimethylsilyloxyethene catalyzed by lanthanide/pybox complexes
    Desimoni, Giovanni
    Faita, Giuseppe
    Piccinini, Francesca
    Toscanini, Marco
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (23) : 5228 - 5230
  • [25] Recent progress in lanthanide-catalyzed organic reactions in protic media
    Luo, SZ
    Zhang, BL
    Xian, M
    Jañczuk, A
    Xie, WH
    Cheng, JP
    Wang, PG
    CHINESE SCIENCE BULLETIN, 2001, 46 (20): : 1673 - 1681
  • [26] Stereoselectivity in (Acyloxy)borane-Catalyzed Mukaiyama Aldol Reactions
    Lee, Joshua M.
    Zhang, Xin
    Norrby, Per-Ola
    Helquist, Paul
    Wiest, Olaf
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (13): : 5314 - 5321
  • [27] Enantioselective synthesis of polyketide segments through vinylogous Mukaiyama aldol reactions
    Simsek, Serkan
    Kalesse, Markus
    TETRAHEDRON LETTERS, 2009, 50 (26) : 3485 - 3488
  • [28] Development of Chiral Catalysts for Mukaiyama Aldol Reactions in Aqueous Media
    Kitanosono, Taku
    Kobayashi, Shu
    CHEMICAL RECORD, 2014, 14 (01): : 130 - 143
  • [29] Diastereoselective and enantioselective Mukaiyama aldol reactions of α-ketoesters using hydrogen bond catalysis
    Gondi, Vijaya Bhasker
    Hagihara, Koji
    Rawal, Viresh H.
    CHEMICAL COMMUNICATIONS, 2010, 46 (06) : 904 - 906
  • [30] Tandem Mukaiyama Michael-aldol reactions catalyzed by samarium diiodide
    Giuseppone, N
    Courtaux, Y
    Collin, J
    TETRAHEDRON LETTERS, 1998, 39 (43) : 7845 - 7848
12345