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

doi:10.6023/cjoc201205003

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (07): 1159-1168.DOI: 10.6023/cjoc201205003 Previous Articles Next Articles

ACCOUNT

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

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 发布日期:2012-05-23
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. 20872063; 21072100);高等学校博士点基金(No. 20110031110012)资助项目.

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

Xu Silong, He Zhengjie

State Key Laboratory of Elemento-Organic Chemistry and Department of Chemistry, Nankai University, Tianjin 300071

Received:2012-05-03 Revised:2012-05-19 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).

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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Xu Silong, He Zhengjie. Studies on Reactivity of in situ Generated Allylic Phosphorus Ylides with Aldehydes[J]. Chin. J. Org. Chem., 2012, 32(07): 1159-1168.

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原位生成的烯丙基磷叶立德与醛的化学反应性研究

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

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