title: Integration of electrooxidative cyclization and chemical oxidation via alkoxysulfonium ions. Synthesis of exocyclic ketones from alkenes with cyclization.
abstract: An integration of electrooxidative cyclization and chemical oxidation was achieved. Electrochemical oxidation of alkenes having a nucleophilic moiety in the presence of DMSO gave cyclized alkoxysulfonium ions, which were converted to the corresponding ketones by treatment with triethylamine in a one-pot sequential manner. The method is also an effective tool for cyclization of 1,6-dienes affording five-membered ring diketones in high stereoselectivity.
authors.affiliation: Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, Japan.
authors.forename: Yosuke
authors.initials: Y
authors.lastname: Ashikari
authors.forename: Toshiki
authors.initials: T
authors.lastname: Nokami
authors.forename: Jun-ichi
authors.initials: J
authors.lastname: Yoshida
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D055664:Electrochemical Techniques; D007477:Ions / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000475:Alkenes; D007477:Ions; D007659:Ketones; D013438:Sulfhydryl Compounds