Copper-catalyzed rearrangement of vinyl oxiranes

…, CE McInnis, JT Njardarson

Index: Batory, Lindsay A.; McInnis, Christine E.; Njardarson, Jon T. Journal of the American Chemical Society, 2006 , vol. 128, # 50 p. 16054 - 16055

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Citation Number: 43

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 ...