title: Synthesis of Substituted 1,4-Dioxenes through O-H Insertion and Cyclization Using Keto-Diazo Compounds.
abstract: 1,4-Dioxenes present interesting potential as synthetic intermediates and as unusual motifs for incorporation into biologically active compounds. Here, an efficient synthesis of functionalized 1,4-dioxenes is achieved in two steps. Using keto-diazo compounds, a ruthenium catalyzed O-H insertion with β-halohydrins followed by treatment with base results in cyclization with excellent selectivity, through O-alkylation of the keto-enolate. A variety of halohydrins and anion-stabilizing groups in the diazo-component are tolerated, affording novel functionalized dioxenes. Enantioenriched β-bromohydrins provide enantioenriched 1,4-dioxenes.
authors.affiliation: Department of Chemistry, Imperial College London , South Kensington, London SW7 2AZ, U.K.
authors.forename: Owen A
authors.initials: OA
authors.lastname: Davis
authors.affiliation: Department of Chemistry, Imperial College London , South Kensington, London SW7 2AZ, U.K.
authors.forename: Rosemary A
authors.initials: RA
authors.lastname: Croft
authors.affiliation: Department of Chemistry, Imperial College London , South Kensington, London SW7 2AZ, U.K.
authors.forename: James A
authors.initials: JA
authors.lastname: Bull