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, and Department of Chemistry, Eastern Illinois University, 600 Lincoln Avenue, Charleston, Illinois 61920-3099
Org. Lett., 2007, 9 (7), pp 1175–1178
DOI: 10.1021/ol062539t
Publication Date (Web): March 1, 2007
Copyright © 2007 American Chemical Society

 Oakland University.

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 Eastern Illinois University.

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*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, dembinsk@oakland.edu

Abstract

Abstract Image

5-Endo-dig cycloisomerization of 1,4-di- and 1,2,4-trisubstituted but-3-yn-1-ones in the presence of a catalytic amount of zinc chloride (10 mol %) in dichloromethane at room temperature (22 °C) provides 2,5-di- and 2,3,5-trisubstituted furans in high yields (85−97%).

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History

  • Published In Issue March 29, 2007
  • Received October 15, 2006

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