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