Citation: Yu Lu, Cheng Yuyu, Li Rou, Jiao Yanhua, Li Pengfei. Tandem Cyclization Reaction between Optically Active γ-Nitro Ketone and Chalcone towards the Synthesis of Chiral Cyclohexane Skeletons Bearing Five Stereocenters[J]. Chinese Journal of Organic Chemistry, ;2016, 36(7): 1572-1579. doi: 10.6023/cjoc201605006 shu

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

Yu Lu ^a ,
Cheng Yuyu ^a ,
Li Rou ^a ,
Jiao Yanhua ^b,*,, ,
Li Pengfei ^a,*,,

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

Corresponding author: Jiao Yanhua, yhjiao@hznu.edu.cn Li Pengfei, lipf@sustc.edu.cn;flyli1980@gmail.com
Received Date: 4 May 2016
Revised Date: 31 May 2016

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

Figures(3)

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.
- nitro ketone,
- chalcone,
- tandem cyclization reaction,
- cyclohexane
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