Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (8): 2926-2933.DOI: 10.6023/cjoc202303021 Previous Articles     Next Articles


张素珍a,b, 张文文b, 杨慧b, 顾庆b,*(), 游书力b,*()   

  1. a 上海理工大学材料与化学学院 上海 200093
    b 中国科学院上海有机化学研究所 金属有机化学国家重点实验室 上海 200032
  • 收稿日期:2023-03-15 修回日期:2023-03-28 发布日期:2023-04-07
  • 基金资助:
    国家自然科学基金(21821002); 国家自然科学基金(92256302); 国家自然科学基金(22071260)

Rhodium-Catalyzed Enantioselective Spiroannulation of 2-Alkenylphenols with Alkynes

Suzhen Zhanga,b, Wenwen Zhangb, Hui Yangb, Qing Gub(), Shuli Youb()   

  1. a School of Material and Chemistry, University of Shanghai for Science and Technology, Shanghai 200093
    b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2023-03-15 Revised:2023-03-28 Published:2023-04-07
  • Contact: *E-mail:,
  • Supported by:
    The National Natural Science Foundation of China(21821002); The National Natural Science Foundation of China(92256302); The National Natural Science Foundation of China(22071260)

Rh-catalyzed enantioselective spiroannulation of 2-alkenylphenols with alkynes was developed. In the presence of 5 mol% BINOL-derived (BINOL: 1,1'-bi-2,2'-naphthol) cyclopentadiene-Rh complex [(R)-CpRh1] and 2 equiv. of Cu(O- Ac)2, the C—H activation/annulation reaction proceeded smoothly to afford a wide range of enantioenriched spirocyclohexenones in up to 84% yield and 81% ee. This reaction features mild reaction conditions and good functional group tolerance.

Key words: 2‑alkenylphenol, alkyne, cyclopentadiene-Rh complex, spiroannulation, spirocyclohexenone