Synthesis of new chiral [2-(1-hydroxyalkyl)pyrrolidino]methylferrocenes and application to the catalytic asymmetric addition of diethylzinc to arylaldehydes

被引:5
|
作者
Xu, CL [1 ]
Wang, MC [1 ]
Hou, XH [1 ]
Liu, HM [1 ]
Wang, DH [1 ]
机构
[1] Zhengzhou Univ, Dept Chem, Zhengzhou 450052, Peoples R China
关键词
chiral [2-(1-hydroxyalkyl)pyrrolidino]methylferrocene; synthesis; asymmetric addition; diethylzinc; arylaldehyde;
D O I
10.1002/cjoc.200591443
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of new optically active [2-(1-hydroxyalkyl)pyrrolidino]methylferrocenes were conveniently prepared from commercially available L-proline and ferrocenecarboxylic acid. The crystal structure of key intermediate was obtained. They were then applied to catalyze enantioselective addition of diethylzinc to arylaldehydes with enantioselectivity up to 99%. The effects of the ligand structures on the enantioselectivity were also studied.
引用
收藏
页码:1443 / 1448
页数:6
相关论文
共 50 条
  • [41] VINYL ANION EQUIVALENTS .4. EFFICIENT SYNTHESIS OF 2-(1-HYDROXYALKYL)-2-CYCLOPENTEN-1-ONES
    KUSUDA, S
    UENO, Y
    TORU, T
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (09) : 2720 - 2724
  • [42] Asymmetric synthesis of 5-(1-hydroxyalkyl)-5-methyl-5H-furan-2-ones
    Bruyère, H
    Ballereau, S
    Selkti, M
    Royer, J
    TETRAHEDRON, 2003, 59 (31) : 5879 - 5886
  • [43] Synthesis of new chiral aliphatic amino diselenides and their application as catalysts for the enantioselective addition of diethylzinc to aldehydes
    Braga, AL
    Paixao, MW
    LUdtke, DS
    Silveira, CC
    Rodrigues, OED
    ORGANIC LETTERS, 2003, 5 (15) : 2635 - 2638
  • [44] Enantioselective synthesis and use in catalytic asymmetric addition of diethylzinc to benzaldehyde of new chiral cyclic hydroxyamino ferrocene and chromium complexes:: influence of the complexation on the enantioselectivity
    Malfait, S
    Pélinski, L
    Brocard, J
    TETRAHEDRON-ASYMMETRY, 1998, 9 (15) : 2595 - 2610
  • [45] Synthesis of novel chiral bidentate hydroxyalkyl-N-heterocyclic carbene ligands and their application in palladium-catalyzed Mizoroki-Heck couplings and asymmetric addition of diethylzinc to benzaldehyde
    Faraji, Laleh
    Jadidi, Khosrow
    Notash, Behrouz
    TETRAHEDRON LETTERS, 2014, 55 (02) : 346 - 350
  • [46] The synthesis of silica-supported chiral BINOL: Application in Ti-catalyzed asymmetric addition of diethylzinc to aldehydes
    Pathak, Kavita
    Ahmad, Irshad
    Abdi, Sayed H. R.
    Kureshy, Rukhsana I.
    Khan, Noor-ul H.
    Jasra, Raksh V.
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2008, 280 (1-2) : 106 - 114
  • [47] Enantiopure inherently chiral calix[4]arene derivatives containing quinolin-2-yl-methanol moiety: Synthesis and application in the catalytic asymmetric addition of diethylzinc to benzaldehyde
    Ru Miao
    ZhenXiang Xu
    ZhiTang Huang
    ChuanFeng Chen
    Science in China Series B: Chemistry, 2009, 52 : 505 - 512
  • [48] Preparation of new chiral polymers possessing N-ferrocenylmethyl-ephedrine and their application as chiral catalysts to the asymmetric addition of diethylzinc to aldehyde
    Watanabe, Makoto
    Araki, Shuki
    Butsugan, Yasuo
    Uemura, Masaru
    Chemistry Express, 1990, 5 (10):
  • [49] Enantiopure inherently chiral calix[4]arene derivatives containing quinolin-2-yl-methanol moiety: Synthesis and application in the catalytic asymmetric addition of diethylzinc to benzaldehyde
    Miao Ru
    Xu ZhenXiang
    Huang ZhiTang
    Chen ChuanFeng
    SCIENCE IN CHINA SERIES B-CHEMISTRY, 2009, 52 (04): : 505 - 512
  • [50] Synthesis of new chiral catalysts, 2-azanorbornyloxazolidines, for enantioselective addition of diethylzinc to aldehydes
    Nakano, H
    Okuyama, Y
    Iwasa, K
    Hongo, H
    HETEROCYCLES, 2001, 54 (01) : 411 - 418