A tandem reaction initiated by 1,4-addition of bis(iodozincio)methane for 1,3-diketone formation

J Am Chem Soc. 2010 Jan 20;132(2):432-3. doi: 10.1021/ja910428y.

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.

MeSH terms

  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Ketones
  • bis(iodozincio)methane
  • Methane