Acta Chim. Sinica ›› 2016, Vol. 74 ›› Issue (2): 130-148.DOI: 10.6023/A15090617 Previous Articles     Next Articles



杨丽军, 马军安   

  1. 天津大学化学系 天津化学化工协同创新中心 天津 300072
  • 投稿日期:2015-09-22 发布日期:2016-02-22
  • 通讯作者: 马军安
  • 基金资助:


New Advances on Nucleophilic Phosphine-Triggered Annulation Reactions of Allenoates

Yang Lijun, Ma Junan   

  1. Department of Chemistry, Tianjin University and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072
  • Received:2015-09-22 Published:2016-02-22
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21225208, 21532008), the National Basic Research Program of China (973 Program, No. 2014CB745100), and Tianjin Municipal Science & Technology Commission (No. 14JCZDJC33400).

In the mid 1990s, Lu and co-workers reported the nucleophilic phosphine-triggered annulation reactions of allenoates with electron-deficient olefins or imines. As one of the most efficient and straightforward synthetic strategies for the construction of highly functionalized carbocycle or heterocycle structural motifs, the development and application of nucleophilic phosphine-triggered annulation of allenoates by using various nucleophilic phosphines and electron-deficient partners have attracted more and more interests of chemists over the past decades. Furthermore, the development of asymmetric phosphine-triggered annulation of allenoates cleaved a new way to the total synthesis of bioactive natural products and medicinally important substances. In addition, aldehydes and ketones were also employed into this reaction, leading to a wide range of O-fused heterocycles. This review focuses on the important developments concerning racemic and asymmetric annulation reactions of allenoates in the past two decades.

Key words: nucleophilic phosphine, allenoate, annulation reaction, Lu Reaction, zwitterionic intermediate