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  • Title: A tandem reaction initiated by 1,4-addition of bis(iodozincio)methane for 1,3-diketone formation.
    Author: Sada M, Matsubara S.
    Journal: J Am Chem Soc; 2010 Jan 20; 132(2):432-3. PubMed ID: 20028127.
    Abstract:
    Treatment of an gamma-acyloxy-alpha,beta-unsaturated ketone with bis(iodozincio)methane leads to a novel tandem reaction consisting of three steps: (1) 1,4-addition of the dizinc reagent to the enone, which affords the corresponding zinc enolate of the beta-zinciomethylated ketone; (2) intramolecular nucleophilic attack by the enolate on the ester group; and (3) Grob-type fragmentation of the adduct, accompanied by elimination of the zinc alkoxide of allyl alcohol. The overall reaction gives 1,3-diketones efficiently.
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