Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (3): 1084-1090.DOI: 10.6023/cjoc202301011 Previous Articles     Next Articles

Special Issue: 中国女科学家专辑



戴春波, 夏思奇, 陈晓玉, 杨丽敏*()   

  1. 杭州师范大学材料与化学化工学院 有机硅化学及材料技术教育部重点实验室 杭州 311121
  • 收稿日期:2023-01-10 修回日期:2023-02-20 发布日期:2023-02-27
  • 通讯作者: 杨丽敏
  • 作者简介:
    † 共同第一作者.
  • 基金资助:
    国家自然科学基金(22271071); 浙江省自然科学基金(LY20B020010)

N-Heterocyclic Carbene (NHC)-Catalyzed [4+3] Cycloaddition to Synthesize 4-Aminobenzoheptenolactons

Chunbo Dai, Siqi Xia, Xiaoyu Chen, Limin Yang()   

  1. Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121
  • Received:2023-01-10 Revised:2023-02-20 Published:2023-02-27
  • Contact: Limin Yang
  • About author:
    † These authors contributed equally to this work.
  • Supported by:
    National Natural Science Foundation of China(22271071); Natural Science Foundation of Zhejiang Province(LY20B020010)

A highly efficient N-heterocyclic carbene (NHC) catalyzed formal [3+4] cycloaddition reaction of γ-chloroenal with iminoquinones has been developed, producing 4-aminobenzoheptenolactone derivatives in good yields. In order to explore the role of nitroheterocyclic carbene in the site selectivity of the reaction, a theoretical study was carried out using density functional theory. The study showed that the deformation force was the main reason for the difference in site selection.

Key words: N-heterocyclic carbene (NHC), organocatalysis, [4+3] cycloaddition, site selectivity, 4-aminobenzoheptenolactone