Enantioselective benzoin condensation catalyzed by spirocyclic terpene-based N-heterocyclic carbenes

被引:12
|
作者
Rafinski, Zbigniew [1 ]
机构
[1] Nicolaus Copernicus Univ Torun, Fac Chem, 7 Gagarin St, PL-87100 Torun, Poland
关键词
N-Heterocyclic carbenes; Benzoin condensation; Asymmetric synthesis; Acyloins; Terpenoids; TRIAZOLIUM SALTS; THIAZOLIUM;
D O I
10.1016/j.tet.2016.02.049
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of new chiral spirocyclic triazolium salts, derived from (1S)-fenchone and (1R)-camphorquinone, are described. These salts, which are N-heterocyclic carbene precatalysts, were successfully employed in the catalytic asymmetric benzoin condensation affording acyloins with good yields and moderate enantioselectivities. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1860 / 1867
页数:8
相关论文
共 50 条
  • [31] Progress of Organic Reactions Catalyzed by N-Heterocyclic Carbenes
    Wang, Ao
    Xiao, Yonglong
    Zhou, Yu
    Xu, Jinyi
    Liu, Hong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (10) : 2590 - 2608
  • [32] N-Heterocyclic carbenes
    Cazin, Catherine S. J.
    DALTON TRANSACTIONS, 2013, 42 (20) : 7254 - 7254
  • [33] N-heterocyclic carbenes
    Herrmann, WA
    Kocher, C
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (20) : 2162 - 2187
  • [34] Hydroacylation of activated ketones catalyzed by N-heterocyclic carbenes
    Chan, A
    Scheidt, KA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (14) : 4558 - 4559
  • [35] N-Heterocyclic Carbenes
    Schmidt, Andreas
    Wiechmann, Sascha
    Otto, Christian F.
    HETEROCYCLIC CHEMISTRY IN THE 21ST CENTURY: A TRIBUTE TO ALAN KATRITZKY, 2016, 119 : 143 - 172
  • [36] N-Heterocyclic carbenes
    Nolan, Steven P.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 2474 - 2475
  • [37] Hydroacylation of activated ketones catalyzed by N-heterocyclic carbenes
    Chan, Audrey
    Scheidt, Karl A.
    Journal of the American Chemical Society, 2006, 128 (14): : 4558 - 4559
  • [38] Crossed-benzoin condensations utilizing N-heterocyclic carbenes in green solvents
    Barber, Lainey
    Kiddle, James
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [39] NUCLEOPHILIC AROYLATION ON FLUOROQUINAZOLINES CATALYZED BY N-HETEROCYCLIC CARBENES
    Tachikawa, Masashi
    Nakagawa, Mizuki
    Suzuki, Yumiko
    HETEROCYCLES, 2018, 96 (04) : 716 - 732
  • [40] Diastereodivergent Enantioselective [8+2] Annulation of Tropones and Enals Catalyzed by N-Heterocyclic Carbenes
    Wang, Shoulei
    Rodriguez-Escrich, Caries
    Fianchini, Mauro
    Maseras, Feliu
    Pericas, Miguel A.
    ORGANIC LETTERS, 2019, 21 (09) : 3187 - 3192