Tetrahedron

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

AS Demir, A Aybey

Index: Demir, Ayhan S.; Aybey, Asuman Tetrahedron, 2008 , vol. 64, # 49 p. 11256 - 11261

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Citation Number: 7

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, CF3SO3H, and CH2Cl2, at rt gives the corresponding lactones without racemization. The acetoxy ketone moiety migrates selectively in order to ...