有机化学 ›› 2015, Vol. 35 ›› Issue (12): 2568-2574.DOI: 10.6023/cjoc201504022 上一篇    下一篇

研究论文

磺酰胺为烷基化试剂高选择性合成多取代烯烃和2,3-二氢茚衍生物的方法

李海花a,b   

  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 E-mail:lihhtsxy@163.com

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

在质子酸H2SO4催化下, 含β氢醇与磺酰胺反应可高选择性地得到三取代烯烃和2,3-二氢茚衍生物. 含β氢醇酸性条件下脱水后与磺酰胺发生偶联, 可以选择性地合成热力学稳定产物Z-多取代烯烃; 两者发生[3+2]环加成反应, 则可高选择性地得到2,3-二氢茚衍生物.

关键词: 醇, 磺酰胺, 2,3-二氢茚衍生物, 立体选择性, [3+2]环加成

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