A versatile kinetic alkylation-ozonolysis route for the synthesis of lactones: chiral γ-lactones and racemic δ-lactones

Abstract

A robust and versatile kinetic alkylation-ozonolysis procedure, previously used for the synthesis of 2-alkyl-2-cyclopenten-1-ones and racemic γ-substituted-γ-lactones, has now been applied to the synthesis of chiral γ-substituted-γ-lactones and δ-substituted-δ-lactones. In addition to the synthesis of lactones with simple alkyl substituents, the method allows terminal ester and halogen groups, and an alkyne bond to be incorporated into the side chain.