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Synthesis of Enol Lactones via Cu(I)-Catalyzed Intramolecular O-Vinylation of Carboxylic Acids

Changhui Sun, Yewen Fang, Shuang Li, Yue Zhang, Qiwu Zhao, Shana Zhu and Chaozhong Li*

*State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. China, Email: cligmail.sioc.ac.cn

C. Sun, Y. Fang, S. Li, Y. Zhang, Q. Zhao, S. Zhu, C. Li, Org. Lett., 2009, 11, 4084-4087.

DOI: 10.1021/ol9015578 (free Supporting Information)


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Abstract

In the presence of CuI/trans-N,N′-dimethylcyclohexane-1,2-diamine as catalyst, a number of carboxylic acids underwent efficient intramolecular O-vinylation with vinyl bromides leading to the corresponding five- and six-membered enol lactones. The same catalytic system also enabled an efficient cycloisomerization of alkynoic acids.

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Key Words

Lactones


ID: J54-Y2009-2690