Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (10): 4066-4074.DOI: 10.6023/cjoc202104036 Previous Articles     Next Articles

ARTICLES

三价磷介导的分子内环丙烷化反应及环丙烷并[c]香豆素的合成

仇裕鹤a, 鲁康辉a, 韦邦尺a, 潜振凯a, 贺峥杰a,b,*()   

  1. a 南开大学化学学院 元素有机化学国家重点实验室 天津 300071
    b 天津化学化工协同创新中心 天津 300071
  • 收稿日期:2021-04-17 修回日期:2021-05-07 发布日期:2021-06-02
  • 通讯作者: 贺峥杰
  • 作者简介:
    † 共同第一作者
  • 基金资助:
    国家自然科学基金(21472096); 国家自然科学基金(J1103308)

PIII-Mediated Intramolecular Cyclopropanation and Synthesis of Cyclopropa[c]coumarins

Yuhe Qiua, Kanghui Lua, Bangchi Weia, Zhenkai Qiana, Zhengjie Hea,b()   

  1. a State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071
    b Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071
  • Received:2021-04-17 Revised:2021-05-07 Published:2021-06-02
  • Contact: Zhengjie He
  • About author:
    † These authors contributed equally to this work.
  • Supported by:
    National Natural Science Foundation of China(21472096); National Natural Science Foundation of China(J1103308)

Under the treatment of P(NMe2)3, benzoylformates bearing an α,β-unsaturated ketone unit readily underwent an intramolecular cyclopropanation reaction, producing the corresponding cyclopropa[c]coumarins in moderate to good yields. Under the optimized conditions, the reaction exhibited a wide scope of substrates and excellent stereoselectivity, thus provides a facile and efficient method for the synthesis of cyclopropa[c]coumarins.

Key words: benzoylformates, cyclopropanation reaction, cyclopropa[c]coumarins, phosphorus reagent