A tandem reaction of organozinc reagent prepared from palladium-catalyzed umpolung method: diastereoselective formation of cyclohexene derivatives bearing three adjacent stereocenters |
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Authors: | Sada Mutsumi Nomura Kenichi Matsubara Seijiro |
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Institution: | Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku-katsura, Nishikyo, Kyoto 615-8510, Japan. |
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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. |
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