Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (5): 1150-1176.DOI: 10.6023/cjoc201910019 Previous Articles     Next Articles


刘文竹, 豆立娟, 母伟花   

  1. 云南师范大学化学化工学院 昆明 650500
  • 收稿日期:2019-10-13 修回日期:2019-12-23 发布日期:2020-01-15
  • 通讯作者: 母伟花
  • 基金资助:

Recent Progress on[3+2] Ring-Expansion Reaction of Cyclopropane with Unsaturated Compounds

Liu Wenzhu, Dou Lijuan, Mu Weihua   

  1. Faculty of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500
  • Received:2019-10-13 Revised:2019-12-23 Published:2020-01-15
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21763033, 21363028).

Due to its high ring strain, cyclopropanes can react with a variety of unsaturated compounds to construct five- membered carbo- and hetero-cycles through[3+2] ring-expansion reaction. These five-membered compounds are key skeletons of many drugs, natural products and bioactive molecules, and are also an important class of organic intermediates which have wide applications in medicine, agriculture, chemical engineering, organic synthesis and other related areas. Recently, more and more chemists have constructed a lot of complex five-membered carbo- and hetero-cycles by using cyclopropane as a three-carbon synthon, which has promoted the rapid development of focus area. This review summarizes the most recent [3+2] ring-expansion reaction of cyclopropanes with compounds containing unsaturated bonds such as olefins, aldehydes, ketones and nitriles in the past decade. Moreover, the prospects of future development are also discussed.

Key words: cyclopropane, unsaturated bond, [3+2]ring-expansion reaction, five-membered ring