Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts

被引：773
|
作者：
Connon, Stephen J. [1 ]
机构：
[1] Univ Dublin, Ctr Synth & Chem Biol, Sch Chem, Trinity Coll, Dublin 2, Ireland
来源：
CHEMICAL COMMUNICATIONS | 2008年 / 22期
关键词：
D O I：
10.1039/b719249e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Cinchona alkaloid derivatives modified to include a (thio) urea component have emerged in the last three years as readily accessible, robust and tunable bifunctional organocatalysts for a range of synthetically useful transformations. The origins of these catalysts and the major developments in their application in enantioselective synthesis are reviewed.
引用
收藏
页码：2499 / 2510
页数：12
相关论文
共 50 条
  • [1] Recent advances in asymmetric catalysis with cinchona alkaloid-based primary amines
    Jiang, Lin
    Chen, Ying-Chun
    CATALYSIS SCIENCE & TECHNOLOGY, 2011, 1 (03) : 354 - 365
  • [2] Plant Process for the Preparation of Cinchona Alkaloid-Based Thiourea Catalysts
    Wang, Yi
    Milkiewicz, Karen L.
    Kaufman, Mildred L.
    He, Linli
    Landmesser, Nelson G.
    Levy, Daniel V.
    Allwein, Shawn P.
    Christie, Michael A.
    Olsen, Mark A.
    Neville, Christopher J.
    Muthukumaran, Kannan
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2017, 21 (03) : 408 - 413
  • [3] Asymmetric 1,4-Addition of Oxazolones to Nitroalkenes by Bifunctional Cinchona Alkaloid Thiourea Organocatalysts: Synthesis of α,α-Disubstituted α-Amino Acids
    Aleman, Jose
    Milelli, Andrea
    Cabrera, Silvia
    Reyes, Efraim
    Jorgensen, Karl Anker
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (35) : 10958 - 10966
  • [4] Cinchona alkaloid-based chiral catalysts act as highly efficient multifunctional organocatalysts for the asymmetric conjugate addition of malonates to nitroolefins
    Ashokkumar, Veeramanoharan
    Siva, Ayyanar
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (40) : 10216 - 10225
  • [5] Insights into the Dual Activation Mechanism Involving Bifunctional Cinchona Alkaloid Thiourea Organocatalysts: An NMR and DFT Study
    Zhu, Jun-Ling
    Zhang, Yong
    Liu, Chong
    Zheng, An-Min
    Wang, Wei
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (21): : 9813 - 9825
  • [6] Asymmetric Brominative Dearomatization of 2-Naphthols Using a Cinchona Alkaloid-Based Organocatalyst
    Omae, Kouhei
    Miyake, Yoshihiro
    Shimogaki, Mio
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (06): : 4232 - 4236
  • [7] Transition state analogues as mechanistic probes for asymmetric desymmetrization by cinchona alkaloid-based catalysts
    Emmings, Edith
    Hofmeister, Gretchen
    Alberg, David
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [8] Urea- and thiourea-substituted cinchona alkaloid derivatives as highly efficient bifunctional organocatalysts for the asymmetric addition of malonate to nitroalkenes: Inversion of configuration at C9 dramatically improves catalyst performance
    McCooey, SH
    Connon, SJ
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (39) : 6367 - 6370
  • [9] Asymmetric Hydrophosphonylation of α-Ketoesters Catalyzed by Cinchona-Derived Thiourea Organocatalysts
    Wang, Fei
    Liu, Xiaohua
    Cui, Xin
    Xiong, Yan
    Zhou, Xin
    Feng, Xiaoming
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (03) : 589 - 592
  • [10] Cinchona derivatives as bifunctional organocatalysts for the direct asymmetric nitroaldol (Henry) reaction
    Marcelli, T
    van der Haas, RNS
    van Maarseveen, JH
    Hiemstra, H
    SYNLETT, 2005, (18) : 2817 - 2819
12345