Synthesis of chiral acetoxy lactones via the Baeyer–Villiger oxidation of cyclic aromatic acetoxy ketones

Abstract

The α-acetoxylation of indanones and tetralones by using Mn(OAc) 3 followed by the enzyme catalyzed kinetic resolution of acetoxy ketones furnished both of the enantiomers of α-acetoxy ketones in good chemical and optical yields. The Baeyer–Villiger oxidation of α-acetoxy ketones with m-CPBA, CF 3SO 3H, and CH 2Cl 2, at rt gives the corresponding lactones without racemization. The acetoxy ketone moiety migrates selectively in order to form lactones. The mild hydrolysis of lactones affords phenolic α-hydroxycarboxylic acid derivatives.