Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (12): 2568-2574.DOI: 10.6023/cjoc201504022 Previous Articles     Next Articles




  1. a 唐山学院环境与化学工程系 唐山 063000;
    b 唐山市微纳米材料制备及应用重点实验室 唐山 063000
  • 收稿日期:2015-04-15 修回日期:2015-06-18 发布日期:2015-08-25
  • 通讯作者: 李海花

High Regio- and Stereo-selective Synthesis of Polysubstituted Alkenes and Indane Derivatives Using N-Benzylic Sulfonamides as Alkylating Agents

Li Haihuaa,b   

  1. a Department of Environmental and Chemical Engineering, Tangshan College, Tangshan 063000;
    b Key Laboratory of Micro-nano-material Preparation and Application of Tangshan City, Tangshan 063000
  • Received:2015-04-15 Revised:2015-06-18 Published:2015-08-25

The reaction of alcohols with β-hydrogen and N-benzylic sulfonamide has been developed in the presence of H2SO4 for the synthesis of polysubstituted alkenes and indane derivatives with high stereoselectivity. Alcohol with β-hydrogen dehydrates and then couples with N-benzylic sulfonamide in the acidic conditions to selectively synthesize thermodynamic stability product Z-multisubstituted alkenes, which then lead to a [3+2] annulation reaction to selectively afford the indane derivatives.

Key words: alcohol, N-benzylic sulfonamide, indane derivative, stereoselectivity, [3+2] annulation reaction