Citation: Zhang Yang, Xing Fen, Feng Zenan, Du Guangfen, Gu Chengzhi, He Lin. N-Heterocyclic Carbene-Catalyzed Double Michael Addition of Cyano Acetates and Dienones: Diastereoselective Synthesis of Multisubstituted Cyclohexanones and Indanes[J]. Chinese Journal of Organic Chemistry, ;2020, 40(6): 1608-1617. doi: 10.6023/cjoc202002012 shu

N-Heterocyclic Carbene-Catalyzed Double Michael Addition of Cyano Acetates and Dienones: Diastereoselective Synthesis of Multisubstituted Cyclohexanones and Indanes

School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832000

Corresponding author: Du Guangfen, duguangfen@shzu.edu.cn He Lin, helin@shzu.edu.cn
Received Date: 11 February 2020
Revised Date: 14 March 2020
Available Online: 31 March 2020
Fund Project: the National Natural Science Foundation of China 21662029Project supported by the National Natural Science Foundation of China (No. 21662029)

Figures(3)

The unique Brønsted basic character of N-heterocyclic carbenes (NHCs) has been used to catalyze the double Michael addition between dienones and cyanoacetates. In the presence of 10 mol% NHC, divinyl ketones reacted with cyano acetates to produce multisubstituted cyclohexanones in 60%~89% yields with 5:1~>20:1 dr. Under the same conditions, benzenedi(enones) underwent double Michael addition with cyano acetates or malononitrile to construct multisubstituted indanes in 77%~98% yields and >20:1 dr.
- N-heterocyclic carbenes,
- Michael addition,
- Brønsted base,
- cyclohexanone,
- indane
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