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Communication

Copper-Catalyzed Rearrangement of Vinyl Oxiranes

Supporting Info

Lindsay A. Batory, Christine E. McInnis, and Jon T. Njardarson*

Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301

J. Am. Chem. Soc., 2006, 128 (50), pp 16054–16055

DOI: 10.1021/ja067073o

Publication Date (Web): November 23, 2006

Abstract

A novel copper-catalyzed vinyl oxirane ring expansion protocol has been developed. A wide range of vinyl oxiranes can be rearranged to 2,5-dihydrofurans in excellent yields in the presence of electrophilic copper(II) acetylacetonate catalysts. Regioisomeric vinyl oxiranes can be converted to a single dihydrofuran product using these conditions. This method uses low catalyst loadings (0.5−5 mol %), has good tolerance of substitution patterns, and can be done in the absence of solvent.

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