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A Tandem Reaction Initiated by 1,4-Addition of Bis(iodozincio)methane for 1,3-Diketone Formation

Mutsumi Sada and Seijiro Matsubara*

*Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku-katsura, Nishikyo, Kyoto 615-8510, Japan, Email: matsubarorgrxn.mbox.media.kyoto-u.ac.jp

M. Sada, S. Matsubara, J. Am. Chem. Soc., 2010, 132, 432-433.

DOI: 10.1021/ja910428y


Abstract

Treatment of an γ-acyloxy-α,β-unsaturated ketone with bis(iodozincio)methane leads to a novel tandem reaction consisting of three steps: 1,4-addition of the dizinc reagent to the enone, intramolecular nucleophilic attack by the enolate on the ester group, and Grob-type fragmentation of the adduct to give 1,3-diketones efficiently.

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proposed mechanism



Key Words

1,3-Diketones, Grob Fragmentation


ID: J48-Y2010-0160