ABSTRACT γ–Hydroxy enones are reactive synthetic building blocks that can be utilized in the synthesis of a range of biologically important compounds. cis γ–Hydroxy enones readily cyclize to hemi-acetals that can readily dehydrate to furnish substituted furans. While there exists many methods for the construction of the γ–hydroxy enone subunit, control of the reaction conditions is critical so that furanization does not occur. Recently, the 1,2-dioxine moiety has proven itself as a effective masking group of the cis γ–hydroxy enone. Trapping of the cis γ–hydroxy enone has been accomplished via 1,4-conjugate addition by a range of stabilized nucleophiles to yield highly substituted cyclopropanes and γ-lactones. Additionally, via the use of transition metal mediated homolytic ring-opening of 1,2-dioxines, enantio-enriched cis γ–hydroxy enones have been generated which have consequently furnished enantio-enriched cyclopropanes and γ–lactones.
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