A facile synthesis and asymmetric catalytic activity of new 3-substituted chiral BINOL ligands

被引:3
|
作者
Liu, Bing [1 ,2 ]
Fang, Cao [1 ]
Dong, Zhi-Bing [1 ]
Li, Jin-Shan [1 ]
机构
[1] Nankai Univ, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R China
[2] Tianjin Univ Sci & Technol, Fac Food Engn & Biotechnol, Tianjin Key Lab Food Nutr & Safety, Tianjin 300457, Peoples R China
关键词
BINOL; 1,2,3-benzotriazole; imidazole; diethylzinc; asymmetric addiotion;
D O I
10.1002/aoc.1350
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Three new chiral ligands, (S)-3-(1H-imidazol-1-yl)methyl-1,1'-binaphthol [(S)-1], (S)-3-(1H-1,2,3-benzotriazol-1-yl)methyl-1,1'-binaphthol [(S)-2] and (S)-3-(2H-1,2,3-benzotriazol-2-yl)methyl-1,1'-binaphthol [(S)-3], were prepared by a simple method. They showed moderate catalytic properties for the asymmetric addition of diethylzinc to benzaldehyde in the presence of titanium tetraisopropoxide. Copyright (C) 2008 John Wiley & Sons, Ltd.
引用
收藏
页码:55 / 58
页数:4
相关论文
共 50 条
  • [31] Chiral imidates as a new class of nitrogen-based chiral ligands: synthesis and catalytic activity in asymmetric aziridinations and diethylzinc additions
    Noel, Timothy
    Vandyck, Koen
    Robeyns, Koen
    Van Meervelt, Luc
    Van der Eycken, Johan
    TETRAHEDRON, 2009, 65 (43) : 8879 - 8884
  • [32] N-substituted amides as chiral ligands for catalytic asymmetric reactions
    Zhang, J
    Zhou, HB
    Xie, RG
    CURRENT ORGANIC CHEMISTRY, 2002, 6 (10) : 865 - 890
  • [33] FACILE SYNTHESIS OF 3-SUBSTITUTED CHROMONES FROM AN ENAMINOKETONE
    YOKOE, I
    MARUYAMA, K
    SUGITA, Y
    HARASHIDA, T
    SHIRATAKI, Y
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1994, 42 (08) : 1697 - 1699
  • [34] Catalytic asymmetric synthesis of homoallylic alcohols: Chiral amplification and chiral poisoning in a titanium/BINOL catalyst system
    Faller, JW
    Sams, DWI
    Liu, X
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (05) : 1217 - 1218
  • [35] Asymmetric synthesis of 3-substituted unsaturated prolines from chiral sulfoximine substituted allyl titanium(IV) complexes
    Tiwari, SK
    Schneider, A
    Koep, S
    Gais, HJ
    TETRAHEDRON LETTERS, 2004, 45 (45) : 8343 - 8346
  • [36] Asymmetric synthesis of 3-substituted pyrrolidones via α-alkylation of a chiral non-racemic γ-lactam
    Baussanne, I
    Travers, C
    Royer, J
    TETRAHEDRON-ASYMMETRY, 1998, 9 (05) : 797 - 804
  • [37] Pd-Catalyzed Asymmetric Allylic Alkylations of 3-Substituted Indoles Using Chiral P/Olefin Ligands
    Liu, Yilin
    Du, Haifeng
    ORGANIC LETTERS, 2013, 15 (04) : 740 - 743
  • [38] SYNTHESIS AND POLYMERIZATION OF THIOPHENES 3-SUBSTITUTED BY CHIRAL CHAINS
    SCHULZ, E
    BETHMONT, V
    FAHMI, K
    FACHE, F
    LEMAIRE, M
    JOURNAL DE CHIMIE PHYSIQUE ET DE PHYSICO-CHIMIE BIOLOGIQUE, 1995, 92 (04) : 783 - 786
  • [39] An Efficient Direct Asymmetric Synthesis of 3-Substituted Phthalides
    Zhang, Zhan-Bin
    Lu, Yong-Qin
    Duan, Xin-Fang
    SYNTHESIS-STUTTGART, 2011, (21): : 3435 - 3438
  • [40] BIOMIMETIC ASYMMETRIC SYNTHESIS OF 3-SUBSTITUTED DIHYDROISOCARBOSTYRIL DERIVATIVES
    WAKABAYASHI, T
    WATANABE, K
    HETEROCYCLES, 1978, 9 (01) : 80 - 80