有机化学 ›› 2014, Vol. 34 ›› Issue (12): 2438-2447.DOI: 10.6023/cjoc201407027 上一篇    下一篇

综述与进展

烯丙基磷叶立德与羰基化合物的Vinylogous类型有机反应研究进展

徐四龙a, 贺峥杰b   

  1. a. 西安交通大学理学院化学系 西安 710049;
    b. 南开大学元素有机化学国家重点实验室 天津化学化工协同创新中心 天津 300071
  • 收稿日期:2014-07-16 修回日期:2014-08-11 发布日期:2014-08-26
  • 通讯作者: 贺峥杰 E-mail:zhengjiehe@nankai.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21272119,21121002)、高等学校博士点基金(No.20110031110012)、中央高校基本科研基金(No.08143076)和中国博士后科学基金(No.2014M550484)资助项目.

Progress on Vinylogous Organic Reactions of Allylic Phosphorus Ylides with Carbonyl Compounds

Xu Silonga, He Zhengjieb   

  1. a. Department of Chemistry, School of Science, Xi'an Jiaotong University, Xi'an 710049;
    b. State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300071
  • Received:2014-07-16 Revised:2014-08-11 Published:2014-08-26
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21272119, 21121002), the Research Fund for the Doctoral Program of Higher Education of China (No. 20110031110012), the Fundamental Research Funds for the Central Universities (No. 08143076) and the China Postdoctoral Science Foundation (No. 2014M550484).

烯丙基磷叶立德(allylic phosphorus ylides)是一类具有丰富反应性的有机中间体. 由于碳负离子离域, 烯丙基磷叶立德可通过γ位碳负离子参与亲核进攻, 从而实现vinylogous(插烯)类型有机合成反应. 综述了烯丙基磷叶立德与羰基化合物的vinylogous类型反应, 具体包括vinylogous Wittig烯化反应以及多种环化反应. 这些反应拓展了烯丙基磷叶立德在有机合成中的应用, 并提供构筑多种重要有机功能分子的新方法.

关键词: 磷叶立德, 插烯规则, Wittig反应, 环化反应

Allylic phosphorus ylides are a class of important and versatile intermediates in synthetic organic chemistry. Due to the delocalization of the carbanion center, an array of vinylogous organic reactions of allylic phosphorus ylides through γ-attack of the carbanion have been achieved in recent years. This mini-review aims to summarize the vinylogous reactivity of allylic phosphorus ylides toward carbonyl compounds, mainly including vinylogous Wittig reactions and various annulation reactions. These reactions broaden the application of allylic phosphorus ylides in organic chemistry, and also provide new synthetic methods for many important organic molecules.

Key words: phosphorus ylide, vinylogy, Wittig reaction, annulation reaction