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

doi:10.6023/cjoc201605006

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

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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

于璐^a, 程玉宇^a, 李柔^a, 焦艳华^b, 李鹏飞^a

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 E-mail:yhjiao@hznu.edu.cn;lipf@sustc.edu.cn,flyli1980@gmail.com
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

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

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).

1. Tandem Cyclization Reaction between Optically Active γ-Nitro Ketone and Chalcone towards the Synthesis of Chiral Cyclohexane Skeletons Bearing Five Stereocenters.PDF(4119KB)

Abstract

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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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]. Chin. J. Org. Chem., 2016, 36(7): 1572-1579.

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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

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

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