FeCl₃-Catalyzed Nucleophilic Substitution of Propargylic Acetates with Enoxysilanes

Zhuang-ping Zhan,* Xu-bin Cai, Shao-pei Wang, Jing-liang Yu, Hui-juan Liu and Yuan-yuan Cui

*Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, People's Republic of China, Email: zpzhanxmu.edu.cn

Z.-P. Zhang, X.-B. Cai, S.-P. Wang, J.-L. Yu, H.-J. Liu, Y.-Y. Cui, J. Org. Chem., 2007, 72, 9838-9841.

DOI: 10.1021/jo701782g

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Abstract

An efficient FeCl₃-catalyzed substitution reaction of propargylic acetates with enoxysilanes under mild conditions affords corresponding γ-alkynyl ketones. A subsequent TsOH-catalyzed cyclization without purification of the γ-alkynyl ketone intermediates, offers a straightforward synthetic route to tri- or tetrasubstituted furans.

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Key Words

Furans

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ID: J42-Y2007-4090