A facile synthesis and the asymmetric catalytic activity of BINOL-based thiazole (thiadiazole) thioether ligands

被引:8
|
作者
Dong, Zhi-Bing [1 ]
Liu, Bing [1 ]
Fang, Cao [1 ]
Li, Jin-Shan
机构
[1] Nankai Univ, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
BINOL; diethylzinc; titanium tetraisopropoxide; copper trifluoromethanesulfonate; asymmetric addition;
D O I
10.1016/j.jorganchem.2007.10.008
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Four new BINOL-based thiazole (thiadiazole) thioether ligands (S)-1, (S)-2, (SS)-3 and (S)-4 were prepared. When their catalytic effectiveness was tested, good results (up to 93% ee and 97% yield) were obtained in the asymmetric addition of diethylzinc to aldehydes while poor results were obtained in the asymmetric conjugate addition of diethylzinc to enones. (c) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:17 / 22
页数:6
相关论文
共 50 条
  • [21] Synthesis, structures and catalytic activity of some BINOL based boronates and boronium salts
    Garg, Shipra
    Unruh, Daniel K.
    Krempner, Clemens
    DALTON TRANSACTIONS, 2021, 50 (14) : 5044 - 5049
  • [22] Enantioselective copper(II)-catalyzed conjugate addition of diethylzinc to β-substituted enones utilizing BINOL-based phosphoramidite ligands
    Zhao, Wenxian
    Wang, Tao
    Zhao, Ruijuan
    Xie, Huanping
    Liu, Lantao
    TETRAHEDRON-ASYMMETRY, 2016, 27 (4-5) : 157 - 162
  • [23] Synthesis and Catalytic Asymmetric Applications of Quinazolinol Ligands
    Karakaya, Idris
    Karabuga, Semistan
    Mart, Mehmet
    Altundas, Ramazan
    Ulukanli, Sabri
    SYNTHESIS-STUTTGART, 2016, 48 (11): : 1719 - 1726
  • [24] Chiral Sulfur Ligands for Catalytic Asymmetric Synthesis
    Hiroi, Kunio
    Sone, Takanori
    CURRENT ORGANIC SYNTHESIS, 2008, 5 (04) : 305 - 320
  • [25] Facile Synthesis of Chiral Conjugated Polymer Based on BINOL Skeleton
    Chun E DONG
    Yong Gang ZHI
    Zuo Long YU
    Liang Fu ZHANG
    Albert. S. C. CHAN (Chengdu institute of organic chemistry Academ Sinica Chengdu 610041 Hong Kong Polytechnic University
    ChineseChemicalLetters, 2000, (01) : 29 - 30
  • [26] Facile synthesis of chiral conjugated polymer based on BINOL skeleton
    Dong, CE
    Zhi, YG
    Yu, ZL
    Zhang, LF
    Chan, ASC
    CHINESE CHEMICAL LETTERS, 2000, 11 (01) : 29 - 30
  • [27] Manganese(II) coordination compounds of thiazole-hydrazone based NNN-donor ligands: Synthesis, characterization and catalytic activity
    Safikhani-Golboos, Roghaieh
    Ghorbanloo, Massomeh
    Bikas, Rahman
    Sasani, Roya
    Lecki, Jan Grzegorz Ma
    Krawczyk, Marta S.
    Siczek, Mi losz
    INORGANICA CHIMICA ACTA, 2022, 543
  • [28] Facile one-pot synthesis of BINOL- and H8-BINOL-based aryl phosphites and their use in palladium catalysed asymmetric allylation
    Gavrilov, KN
    Lyubimov, SE
    Petrovskii, PV
    Zheglov, SV
    Safronov, AS
    Skazov, RS
    Davankov, VA
    TETRAHEDRON, 2005, 61 (44) : 10514 - 10520
  • [29] Synthesis and antimicrobial activity of new thiazole and thiadiazole derivatives via ethyl pyruvate
    Saleh, Fatma M.
    Abdelhamid, Abdou O.
    Hassaneen, Hamdi M.
    JOURNAL OF SULFUR CHEMISTRY, 2020, 41 (02) : 130 - 145
  • [30] A novel BINOL-based cyclophane via click chemistry: synthesis and its applications for sensing silver ions
    Hou, Ji-Ting
    Zhang, Qin-Fang
    Xu, Bang-Yu
    Lu, Qiao-Sen
    Liu, Qiang
    Zhang, Ji
    Yu, Xiao-Qi
    TETRAHEDRON LETTERS, 2011, 52 (38) : 4927 - 4930