有机化学 ›› 2020, Vol. 40 ›› Issue (6): 1608-1617.DOI: 10.6023/cjoc202002012 上一篇    下一篇

研究论文

氮杂环卡宾催化氰基乙酸酯与二烯酮双Michael反应:非对映选择性合成多取代环己酮和茚

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 E-mail:duguangfen@shzu.edu.cn;helin@shzu.edu.cn
  • 基金资助:
    国家自然科学基金(No.21662029)资助项目.

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).

利用氮杂环卡宾(NHC)独特的Brønsted碱性催化二烯酮与氰基乙酸酯的双Michael加成反应.在10 mol% NHC催化下,二乙烯酮可以与氰基乙酸酯反应,以60%~89%的产率和5:1~>20:1的dr值得到多取代环己酮.在相同反应条件下,邻苯二烯酮与氰基乙酸酯和丙二腈等反应,以77%~98%的产率和>20:1的dr值得到多取代茚产物.

关键词: 氮杂环卡宾, Michael加成, Brønsted碱, 环己酮,

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