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2012 , Vol. 32 >Issue 07: 1159 - 1168

DOI: https://doi.org/10.6023/cjoc201205003

研究专题

原位生成的烯丙基磷叶立德与醛的化学反应性研究

  • 徐四龙 ,
  • 贺峥杰
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  • 南开大学化学学院元素有机化学国家重点实验室 天津 300071

收稿日期: 2012-05-03

  修回日期: 2012-05-19

  网络出版日期: 2012-05-23

基金资助

国家自然科学基金(Nos. 20872063; 21072100);高等学校博士点基金(No. 20110031110012)资助项目.

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Studies on Reactivity of in situ Generated Allylic Phosphorus Ylides with Aldehydes

  • Xu Silong ,
  • He Zhengjie
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  • State Key Laboratory of Elemento-Organic Chemistry and Department of Chemistry, Nankai University, Tianjin 300071

Received date: 2012-05-03

  Revised date: 2012-05-19

  Online published: 2012-05-23

Supported by

Project Supported by the National Natural Science Foundation of China (Nos. 20872063, 21072100) and the Research Fund for the Doctoral Program of Higher Education of China (No. 20110031110012).

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摘要

介绍了我们小组最近有关原位生成的烯丙基磷叶立德与醛的化学反应性研究结果. 在化学计量叔膦作用下, 烯丙基碳酸酯或联烯酸酯经原位生成的烯丙基磷叶立德活性中间体, 与醛发生高度立体选择性的三组分Wittig 烯化反应和vinylogous Wittig 烯化反应, 该类反应为合成多取代1,3-二烯衍生物提供了简单、高效的新方法; 在催化量叔膦作用下, γ-甲基联烯酸酯经烯丙基磷叶立德关键中间体与醛发生多个膦催化的环化反应, 为五元、六元含氧杂环化合物的合成提供了原子经济性的方法. 通过氘代实验和核磁跟踪等方法, 对上述反应机理进行了初步探索.

关键词： 磷叶立德; Wittig 反应; vinylogous Wittig 反应; 环化反应

本文引用格式

徐四龙 , 贺峥杰 . 原位生成的烯丙基磷叶立德与醛的化学反应性研究[J]. 有机化学, 2012 , 32(07) : 1159 -1168 . DOI: 10.6023/cjoc201205003

Abstract

This account primarily summarizes our recent work on the reactivity of in situ generated allylic phosphorus ylides with aldehydes. Under the mediation of stoichiometric tertiary phosphines, allylic carbonates or allenoates readily undergo highly stereoselective three-component Wittig and vinylogous Wittig olefination reactions through in situ generated allylic phosphorus ylides. These reactions constitute simple and efficient synthetic methods for polysubstituted 1,3-dienes. Under the catalysis of tertiary phosphines, γ-methyl allenoates chemoselectively undertake several annulations with aldehydes via a key intermediate of allylic phosphorus ylide, providing atom economical synthesis of 5- and 6-membered oxygen heterocycles. By experimental approaches such as deuterium-labeling and NMR monitoring, mechanisms of the above mentioned reactions have also been investigated.

Key words： phosphorus ylide; Wittig reaction; vinylogous Wittig reaction; annulation reaction

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