Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1608-1617.DOI: 10.6023/cjoc202002012 Previous Articles     Next Articles


张阳, 邢芬, 冯泽男, 杜广芬, 顾承志, 何林   

  1. 石河子大学化学化工学院 新疆石河子 832000
  • 收稿日期:2020-02-11 修回日期:2020-03-14 发布日期:2020-03-31
  • 通讯作者: 杜广芬, 何林;
  • 基金资助:

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

Zhang Yang, Xing Fen, Feng Zenan, Du Guangfen, Gu Chengzhi, He Lin   

  1. School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832000
  • Received:2020-02-11 Revised:2020-03-14 Published:2020-03-31
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21662029).

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.

Key words: N-heterocyclic carbenes, Michael addition, Brønsted base, cyclohexanone, indane