Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (7): 1572-1579.DOI: 10.6023/cjoc201605006 Previous Articles     Next Articles



于璐a, 程玉宇a, 李柔a, 焦艳华b, 李鹏飞a   

  1. a. 南方科技大学化学系 深圳 518055;
    b. 杭州师范大学材料与化学化工学院 杭州 310036
  • 收稿日期:2016-05-04 修回日期:2016-05-31 发布日期:2016-06-01
  • 通讯作者: 焦艳华, 李鹏飞;,
  • 基金资助:


Tandem Cyclization Reaction between Optically Active γ-Nitro Ketone and Chalcone towards the Synthesis of Chiral Cyclohexane Skeletons Bearing Five Stereocenters

Yu Lua, Cheng Yuyua, Li Roua, Jiao Yanhuab, Li Pengfeia   

  1. a. Department of Chemistry, South University of Science and Technology of China, Shenzhen 518055;
    b. College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036
  • Received:2016-05-04 Revised:2016-05-31 Published:2016-06-01
  • Supported by:

    Project supported by the Research Grant in 2015 of the South University of Science and Technology of China (No. FRG-SUSTC1501A-57), the National Natural Science Foundation of China (No. 21302089) and the Science and Technology Development Program of Hangzhou (No. 20130533B14).

Chiral cyclohexane motif is widespread in the molecular structures of nature products and medicinal chemicals. And polysubstituted chiral cyclohexanes are important building blocks in organic synthesis. A tandem cyclization via asymmetric induction for the construction of polysubstituted chiral cyclohexane skeletons is described. In the presence of phase-transfer-catalyst, optically active γ-nitro ketone reacted with chalcone smoothly to afford cyclohexane skeletons bearing five consecutive stereocenters in 40%~71% yields with 90%~98% ee. It should be noted that the scope of chalcone is broad. Especially, the asymmetric induction is kept at a high level in each step of the tandem cyclization reaction.

Key words: nitro ketone, chalcone, tandem cyclization reaction, cyclohexane