title: Copper-catalyzed rearrangement of vinyl oxiranes.
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.
authors.affiliation: Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.
authors.forename: Lindsay A
authors.initials: LA
authors.lastname: Batory
authors.forename: Christine E
authors.initials: CE
authors.lastname: McInnis
authors.forename: Jon T
authors.initials: JT
authors.lastname: Njardarson
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D005663:Furans / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D004852:Epoxy Compounds; D005663:Furans; C024370:3,4-epoxy-1-butene; D003300:Copper; D006859:Hydrogen