光学活性γ-硝基酮与查尔酮的串联环化反应构建五手性中心的环己烷骨架
收稿日期: 2016-05-04
修回日期: 2016-05-31
网络出版日期: 2016-06-01
基金资助
南方科技大学2015年科研经费（No.FRG-SUSTC1501A-57）、国家自然科学基金（No.21302089）、杭州市科技发展计划（No.20130533B14）资助项目.
Tandem Cyclization Reaction between Optically Active γ-Nitro Ketone and Chalcone towards the Synthesis of Chiral Cyclohexane Skeletons Bearing Five Stereocenters
Received date: 2016-05-04
Revised date: 2016-05-31
Online 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).
于璐 , 程玉宇 , 李柔 , 焦艳华 , 李鹏飞 . 光学活性γ-硝基酮与查尔酮的串联环化反应构建五手性中心的环己烷骨架[J]. 有机化学, 2016 , 36(7) : 1572 -1579 . DOI: 10.6023/cjoc201605006
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
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