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