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Room Temperature Zinc-Chloride-Catalyzed Cycloisomerization of Alk-3-yn-1-ones: Synthesis of Substituted Furans

Adam Sniady, Audrey Durham, Marco S. Morreale, Kraig A. Wheeler and Roman Dembinski*

*Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, Email: dembinskoakland.edu

A. Sniady, A. Durham, M. S. Morreale, K. A. Wheeler, R. Dembinski, Org. Lett., 2007, 9, 1175-1178.

DOI: 10.1021/ol062539t (free Supporting Information)


Abstract

Zinc chloride-catalyzed 5-endo-dig cycloisomerization of 1,4-di- and 1,2,4-trisubstituted but-3-yn-1-ones in dichloromethane at room temperature provides 2,5-di- and 2,3,5-trisubstituted furans in high yields.

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5-Endo-Dig Electrophilic Cyclization of 1,4-Disubstituted But-3-yn-1-ones: Regiocontrolled Synthesis of 2,5-Disubstituted 3-Bromo- and 3-Iodofurans

A. Sniady, K. A. Wheeler, R. Dembinski, Org. Lett., 2005, 7, 1769-1772.


Key Words

Furans


ID: J54-Y2007-1000