Alkynylsilanes as convenient precursors for the stereoselective synthesis of (E)-disubstituted alkenes

被引:0
|
作者
Zhao, H [1 ]
Cai, MZ [1 ]
机构
[1] Jiangxi Normal Univ, Dept Chem, Nanchang 330027, Peoples R China
关键词
hydromagnesiation; (E)-disubstituted alkene; stereoselective synthesis;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Hydromagneisation of alkynylsilanes 1 gives (Z)-alpha-silylvinyl Grignard reagents 2, which are reacted with alkyl iodides or aryl iodides in the presence of Cul or Pd(PPh3)(4) catalysts to afford (Z)-1,2-disubstituted vinylsilanes 3 in good yields. Intermediates 3 can undergo a desilylation reaction to give (E)-disubstituted alkenes 4 in high yields.
引用
收藏
页码:608 / 610
页数:3
相关论文
共 50 条
  • [41] Direct Synthesis of Disubstituted Trifluoromethylthiolated Alkenes
    Fichez, Jeanne
    Dupommier, Dorian
    Besset, Tatiana
    SYNTHESIS-STUTTGART, 2022, 54 (17): : 3761 - 3770
  • [42] Stereoselective synthesis of 1,4-dienylsilanes via hydromagnesiation of alkynylsilanes
    Zhao, H
    Hao, WY
    Cai, MZ
    Zhou, Z
    JOURNAL OF CHEMICAL RESEARCH, 2003, (12) : 780 - 781
  • [43] Convenient and stereoselective synthesis of (Z)-1-bromo-1-alkenes by microwave-induced reaction
    Kuang, CX
    Senboku, H
    Tokuda, M
    TETRAHEDRON LETTERS, 2001, 42 (23) : 3893 - 3896
  • [44] A convenient synthesis of episulfides and their conversion into alkenes
    Dybowski, P
    Skowronska, A
    SYNTHESIS-STUTTGART, 1997, (10): : 1134 - &
  • [45] VINYLIC ORGANOBORANES .9. A GENERAL STEREOSPECIFIC SYNTHESIS OF (Z)-DISUBSTITUTED AND (E)-DISUBSTITUTED ALKENES VIA ORGANOBORANES
    BROWN, HC
    BASAVAIAH, D
    KULKARNI, SU
    BHAT, NG
    PRASAD, JVNV
    JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (02): : 239 - 246
  • [46] Z:E Selective Preparation of Disubstituted Internal Alkenes and Trisubstituted Alkenes
    Guo Ping
    Zhou Yong
    Zhao Jie
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (03) : 855 - 872
  • [47] Stereoselective Synthesis of Z-Alkenes
    Siau, Woon-Yew
    Zhang, Yao
    Zhao, Yu
    STEREOSELECTIVE ALKENE SYNTHESIS, 2012, 327 : 33 - 58
  • [48] Stereoselective Organocatalytic Synthesis of γ,γ-Disubstituted Butenolides
    Sharma, Vivek
    Bhardwaj, Vimal K.
    Chimni, Swapandeep S.
    CHEMISTRYSELECT, 2018, 3 (19): : 5348 - 5352
  • [49] Stereoselective synthesis of (Z)- or (E)-beta-bromovinyl tellurides and their application in the synthesis of trisubstituted alkenes
    Huang, X
    Wang, YP
    TETRAHEDRON LETTERS, 1996, 37 (41) : 7417 - 7420
  • [50] A convenient stereoselective synthesis of isoamericanol A and isoamericanin A
    She, XG
    Gu, WX
    Wu, TX
    Pan, XF
    SYNTHETIC COMMUNICATIONS, 1999, 29 (15) : 2625 - 2628