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
来源：
TETRAHEDRON | 2016年 / 72卷 / 15期
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
  • [1] Enantioselective benzoin condensation catalyzed by bifunctional N-heterocyclic carbenes
    HUANG XueLiang YE Song Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and Function Institute of Chemistry Chinese Academy of Sciences Beijing China
    Chinese Science Bulletin, 2010, 55 (17) : 1753 - 1757
  • [2] Enantioselective benzoin condensation catalyzed by bifunctional N-heterocyclic carbenes
    Huang XueLiang
    Ye Song
    CHINESE SCIENCE BULLETIN, 2010, 55 (17): : 1753 - 1757
  • [3] Enantioselective benzoin condensation catalyzed by bifunctional N-heterocyclic carbenes
    HUANG XueLiang & YE Song Beijing National Laboratory for Molecular Sciences
    Science Bulletin, 2010, (17) : 1753 - 1757
  • [4] Enantioselective Reactions Catalyzed by N-Heterocyclic Carbenes
    Zhao, Ming
    Zhang, Yu-Tong
    Chen, Jie
    Zhou, Ling
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (01) : 54 - 69
  • [5] An Enantioselective Claisen Rearrangement Catalyzed by N-Heterocyclic Carbenes
    Kaeobamrung, Juthanat
    Mahatthananchai, Jessada
    Zheng, Pinguan
    Bode, Jeffrey W.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (26) : 8810 - +
  • [6] Enantioselective Synthesis of β,γ-Unsaturated α-Fluoroesters Catalyzed by N-Heterocyclic Carbenes
    Zhao, Yu-Ming
    Cheung, Man Sing
    Lin, Zhenyang
    Sun, Jianwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (41) : 10359 - 10363
  • [7] Enantioselective Cycloaddition Reactions of Ketenes Catalyzed by N-Heterocyclic Carbenes
    Chen, Xiang-Yu
    Ye, Song
    SYNLETT, 2013, 24 (13) : 1614 - 1622
  • [8] Highly enantioselective intramolecular Michael additions catalyzed by N-heterocyclic carbenes
    Scheidt, Karl A.
    Phillips, Eric M.
    Wadamoto, Manabu
    Chan, Audrey
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [9] Enantioselective acylation of secondary alcohols catalyzed by chiral N-heterocyclic carbenes
    Kano, T
    Sasaki, K
    Maruoka, K
    ORGANIC LETTERS, 2005, 7 (07) : 1347 - 1349
  • [10] A highly enantioselective intramolecular Michael reaction catalyzed by N-heterocyclic carbenes
    Phillips, Eric M.
    Wadamoto, Manabu
    Chan, Audrey
    Scheidt, Karl A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (17) : 3107 - 3110
12345