title: A tandem reaction of organozinc reagent prepared from palladium-catalyzed umpolung method: diastereoselective formation of cyclohexene derivatives bearing three adjacent stereocenters.
abstract: In the presence of a palladium catalyst, treatment of γ-acyloxy-α,β-unsaturated ketone with bis(iodozincio)methane caused umpolung of π-allylpalladium to give a zinc dienolate. Thus formed zinc species afforded a cyclohexene derivative via a self-condensation reaction. It is noteworthy that the three adjacent stereogenic centers were created in a single process with quite high diastereoselectivity.
authors.affiliation: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku-katsura, Nishikyo, Kyoto 615-8510, Japan.
authors.forename: Mutsumi
authors.initials: M
authors.lastname: Sada
authors.forename: Kenichi
authors.initials: K
authors.lastname: Nomura
authors.forename: Seijiro
authors.initials: S
authors.lastname: Matsubara