Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (6): 2178-2188.DOI: 10.6023/cjoc202210037 Previous Articles     Next Articles


孙李星a, 孙婷婷a, 王海清a, 吴淑芳a, 王小烨c, 刘天雅b,*(), 张宇辰a,*()   

  1. a 江苏师范大学化学与材料科学学院 江苏徐州 221116
    b 徐州医科大学附属医院麻醉科 江苏徐州 221004
    c 徐州医科大学 江苏省麻醉学重点实验室 江苏徐州 221004
  • 收稿日期:2022-10-29 修回日期:2022-12-10 发布日期:2022-12-28
  • 作者简介:
  • 基金资助:
    国家自然科学基金(22101103); 江苏省自然科学基金(BK20201018); 江苏省高层次创新创业人才引进、徐州市科技计划(KC21021); 江苏省大学生创新(202110320041Z)

Lewis Acid-Catalyzed [2+4] Cyclization of 3-Alkyl-2-vinylindoles with α,β-Unsaturated N-Sulfonyl Ketimines

Lixing Suna, Tingting Suna, Haiqing Wanga, Shufang Wua, Xiaoye Wangc, Tianya Liub,*(), Yuchen Zhanga,*()   

  1. a School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
    b Department of Anesthesiology, The Affiliated Hospital of Xuzhou Medical University, Xuzhou, Jiangsu 221004
    c Key Laboratory of Anesthesiology of Jiangsu Province, Xuzhou Medical University, Xuzhou, Jiangsu 221004
  • Received:2022-10-29 Revised:2022-12-10 Published:2022-12-28
  • Contact: E-mail:;
  • About author:
    These authors contributed equally to this work
  • Supported by:
    National Natural Science Foundation of China(22101103); Natural Science Foundation of Jiangsu Province(BK20201018); High-level Innovative and Entrepreneurial Talents Introduction Plan of Jiangsu Province, the Technology Plan of Xuzhou City(KC21021); Undergraduate Students Project of Jiangsu Province(202110320041Z)

A Lewis acid-catalyzed [2+4] cyclization of 3-alkyl-2-vinylindoles with α,β-unsaturated N‑sulfonyl ketimines was established, and indole-containing piperidines with potential antitumor activity were synthesized in moderate to good yields (up to 95% yield) and generally excellent diastereoselectivities (up to>95:5 dr). This work has confronted the challenges in exploring the [2+4] cyclization of 3-alkyl-2-vinylindoles, which will enrich the chemistry of 3-alkyl-2-vinylindoles. In addition, this approach provides an atom-economic method for the synthesis of indole-containing piperidines.

Key words: 3-alkyl-2-vinylindole, α,β-unsaturated N-sulfonyl ketimine, [2+4] cyclization, indole derivative