Synthesis of Substituted Acetylenic Epoxides Followed by Indium-Catalyzed Rearrangement to 2,3,5-Trisubstituted Furans

Jun Yong Kang and Brian T. Connell*

*Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77842-3012, United States, Email: connellchem.tamu.edu

J. Y. Kang, B. T. Connell, J. Org. Chem., 2011, 76, 2379-2383.

DOI: 10.1021/jo2001353

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Abstract

Acetylenic epoxides are directly prepared by nucleophilic ring closure of propargylic alkoxides generated by lithium acetylide addition to α-haloketones. A subsequent, mild and efficient cycloisomerization in the presence of InCl₃ as catalyst delivers 2,3,5-trisubstituted furans.

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Key Words

Epoxides, Furans

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ID: J42-Y2011-1060