Stereoselective reductive radical cyclization of ketonitriles catalyzed by Cp2TiCl2 in the presence of chlorosilane and zinc

被引：32
|
作者：
Zhou, LH [1 ]
Hirao, T [1 ]
机构：
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
来源：
TETRAHEDRON | 2001年 / 57卷 / 32期
基金：
日本学术振兴会;
关键词：
titanium catalyst; one-electron reduction; diastereoselective cyclization; silylating reagent; co-reductant;
D O I：
10.1016/S0040-4020(01)00645-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reductive radical cyclization of ketonitriles was catalyzed by Cp2TiCl2 in the presence Of Me3SiCl, zinc powder and imidazole, giving the 2-amino-3-cyano-2-cyclopenten-1-ols in moderate to good yields with high trans selectivity (up to 94% trans). The influence of the catalyst, chlorosilane, co-reductant, solvent, and temperature on both the yield and diastereoselectivity of the cyclized products was investigated in detail. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：6927 / 6933
页数：7
相关论文
共 50 条
  • [1] Reductive coupling of aldimines mediated with samarium catalyzed by Cp2TiCl2
    Department of Chemistry, Hangzhou University, Hangzhou, 310028, China
    SYNTH. COMMUN., 9 (1483-1486):
  • [2] REDUCTION OF ETHYNES IN THE PRESENCE OF CP2TICL2
    LIU, YY
    CHEN, MW
    ACTA CHIMICA SINICA, 1988, 46 (07) : 703 - 705
  • [3] ISOMERIZATION OF OLEFINS CATALYZED BY CP2TICL2/MG
    QIAN, YL
    LI, GS
    ZHENG, XF
    HUANG, YZ
    JOURNAL OF MOLECULAR CATALYSIS, 1993, 78 (03): : L31 - L35
  • [4] THE ELECTROCHEMICAL REDUCTION OF CP2TICL2 IN THE PRESENCE OF TRIMETHYLPHOSPHINE
    FUSSING, IMM
    PLETCHER, D
    WHITBY, RJ
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 470 (1-2) : 119 - 125
  • [5] Electrocatalytic dehalogenation of α-bromoketones in the presence of Cp2TiCl2
    Nikitin, O. M.
    Gavrilova, G. V.
    Magdesieva, T. V.
    RUSSIAN CHEMICAL BULLETIN, 2007, 56 (05) : 1013 - 1019
  • [6] Electrocatalytic dehalogenation of α-bromoketones in the presence of Cp2TiCl2
    O. M. Nikitin
    G. V. Gavrilova
    T. V. Magdesieva
    Russian Chemical Bulletin, 2007, 56 : 1013 - 1019
  • [7] A novel reduction of diketones with i-RMgBr catalyzed by Cp2TiCl2 and deoxygenation of sulfoxides by Cp2TiCl2/Al system.
    Zhang Y.M.
    Lin M.Q.
    Yu Y.P.
    Journal of Zhejiang University-SCIENCE A, 2004, 5 (10): : 1175 - 1179
  • [8] POLY 195-Cp2TiCl-catalyzed styrene polymerizations initiated by SET reduction of carbonyls: Effect of temperature, aldehyde/Cp2TiCl2 and Cp2TiCl2/Zn ratios
    Asandei, Alexandru D.
    Chen, Yanhui
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
  • [9] Titanium-catalyzed hydrosilylation of olefins: A comparison study on Cp2TiCl2/Sm and Cp2TiCl2/LiAlH4 catalyst system
    Yang, Xiaoling
    Bai, Ying
    Li, Jiayun
    Liu, Yu
    Peng, Jiajian
    Li, Tianbo
    Lang, Rui
    Qiao, Botao
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2019, 194 (1-2) : 64 - 68
  • [10] Science Letters:A novel reduction of diketones with i-RMgBr catalyzed by Cp2TiCl2 and deoxygenation of sulfoxides by Cp2TiCl2/Al system
    张永敏
    林茂钦
    俞永平
    Journal of Zhejiang University Science, 2004, (10) : 9 - 13
12345