New chiral Schiff base as a tridentate ligand for catalytic enantioselective addition of diethylzinc to aldehydes

被引:69
|
作者
Tanaka, Takanori [1 ]
Yasuda, Yorinobu [1 ]
Hayashi, Masahiko [1 ]
机构
[1] Kobe Univ, Fac Sci, Dept Chem, Kobe, Hyogo 6578501, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 18期
关键词
D O I
10.1021/jo060964u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have developed new chiral Schiff base catalysts for the enantioselective addition of diethylzinc reagents to aldehydes. The reaction of benzaldehyde with diethylzinc in the presence of 1 mol % of the chiral Schiff base catalyst proceeded to afford 1-phenyl-1-propanol in 96% enantiomeric excess (ee).
引用
收藏
页码:7091 / 7093
页数:3
相关论文
共 50 条
  • [1] New BINOL Schiff base as a tridentate ligand for catalytic asymmetric addition of diethylzinc to aldehydes in the presence of titanium tetraisopropoxide
    Liu, Bing
    Fang, Cao
    Dong, Zhi-Bing
    Li, Jin-Shan
    [J]. LETTERS IN ORGANIC CHEMISTRY, 2007, 4 (03) : 172 - 174
  • [2] Vasicine as tridentate ligand for enantioselective addition of diethylzinc to aldehydes
    Aga, Mushtaq A.
    Kumar, Brijesh
    Rouf, Abdul
    Shah, Bhahwal A.
    Taneja, Subhash C.
    [J]. TETRAHEDRON LETTERS, 2014, 55 (16) : 2639 - 2641
  • [3] Synthesis of a chiral tridentate ligand from proline and its application to enantioselective addition of diethylzinc to aldehydes
    Qiu, LH
    Shen, ZX
    Ge, JF
    Zhang, YW
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2005, 23 (07) : 898 - 900
  • [4] Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by new chiral oxazolidine ligand
    Kang, YF
    Liu, L
    Wang, R
    Ni, M
    Han, ZJ
    [J]. SYNTHETIC COMMUNICATIONS, 2005, 35 (13) : 1819 - 1823
  • [5] Synthesis of novel chiral tridentate aminophenol ligands for enantioselective addition of diethylzinc to aldehydes
    Yang, Xiao-Feng
    Hirose, Takuji
    Zhang, Guang-You
    [J]. TETRAHEDRON-ASYMMETRY, 2008, 19 (14) : 1670 - 1675
  • [6] New indane derived aminoalcohols as chiral ligands for the catalytic enantioselective addition of diethylzinc to aldehydes
    Sola, L
    VidalFerran, A
    Moyano, A
    Pericas, MA
    Riera, A
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (10) : 1559 - 1568
  • [7] Preparation of chiral aminodiols and their applications in the catalytic enantioselective addition of diethylzinc to aldehydes
    Xu, QY
    Wu, TX
    Pan, XF
    [J]. CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2002, 23 (07): : 1318 - 1320
  • [8] Preparation of Chiral Aminodiols and Their Applications in the Catalytic Enantioselective Addition of Diethylzinc to Aldehydes
    Xu, Qian-Yong
    Wu, Tong-Xing
    Pan, Xin-Fu
    [J]. Kao Teng Hsueh Hsiao Hua Heush Hsueh Pao/ Chemical Journal of Chinese Universities, 2002, 23 (07):
  • [9] New chiral catalysts for the highly enantioselective addition of diethylzinc to aldehydes
    Jin, MJ
    Ahn, SJ
    Lee, KS
    [J]. TETRAHEDRON LETTERS, 1996, 37 (48) : 8767 - 8770
  • [10] Enantioselective addition of diethylzinc to aldehydes catalyzed by ethyl nipecotate-derived new chiral ligand
    Lee, SH
    Im, DS
    Cheong, CS
    Chung, BY
    [J]. HETEROCYCLES, 1999, 51 (08) : 1913 - 1919