Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (8): 2218-2225.DOI: 10.6023/cjoc201903061 Previous Articles     Next Articles

Special Issue: 陈茹玉先生诞辰100周年

Articles

膦催化α'-亚甲基环戊烯酮的形式[6+2]环加成反应

石崇慧, 肖本现, 杜玮, 陈应春   

  1. 四川大学华西药学院 成都 610041
  • 收稿日期:2019-03-27 修回日期:2019-04-29 出版日期:2019-08-25 发布日期:2019-05-21
  • 通讯作者: 陈应春 E-mail:ycchen@scu.edu.cn
  • 基金资助:

    国家自然科学基金(No.21572135)资助项目.

Phosphine-Catalyzed Formal[6+2] Cycloadditions of α'-Methylene 2-Cyclopentenones

Shi Chonghui, Xiao Benxian, Du Wei, Chen Yingchun   

  1. West China School of Pharmacy, Sichuan University, Chengdu 610041
  • Received:2019-03-27 Revised:2019-04-29 Online:2019-08-25 Published:2019-05-21
  • Contact: 10.6023/cjoc201903061 E-mail:ycchen@scu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21572135).

The formal[6+2] cycloaddition reaction of α'-methylene-2-cyclopentenones and 2-alkylidene-1,3-indanediones was developed under the catalysis of tricyclohexyl phosphine, proceeding in a remote γ-regioselective Rauhut-Currier-type reaction followed by a β'-regioselective intramolecular Michael addition process. An array of fused bicyclic frameworks incorperating a spiro-1,3-indanedione motif were produced in fair to good yields of 48%~76% with excellent diastereoseletivity (generally>19:1 dr). This protocol expands the reaction mode of traditional Rauhut-Currier reaction, which might find further application in organic synthesis.

Key words: phosphine catalysis, α'-methylene-2-cyclopentenone, Rauhut-Currier reaction, [6+2]cycloaddition