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Synthesis of α,α-Disubstituted α-Acetoxy Esters and α,α-Disubstituted α- Hydroxy Acids by Baeyer-Villiger Oxidation of the Corresponding β- Ketoesters

[ Vol. 2 , Issue. 1 ]

Author(s):

Henri-Jean Cristau, Xavier Marat, Jean-Pierre Vors, David Virieux and Jean-Luc Pirat   Pages 113 - 119 ( 7 )

Abstract:


The regioselective Baeyer-Villiger oxidation of a wide range of α,ααdisubstituted β-ketoesters has been developed to synthesize, in good yields, α,α-disubstituted α-acetoxy esters. The reactions were performed using m-chloroperbenzoic acid in the presence of triflic acid. The rearrangement was shown to occur with retention of configuration of the migrating group. The corresponding α,ααdisubstituted α-hydroxy acids were obtained in good yields, after hydrolysis.

Keywords:

baeyer-villiger oxidation, ketoesters, m-chloro perbenzoic acid, triflic acid, hydroxy acid

Affiliation:

Laboratoire de Chimie Organique, UMR 5076, Ecole Nationale Supérieure de Chimie de Montpellier, 8, Rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France.



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