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

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

Volume: 2 Issue: 1

Author(s): Henri-Jean Cristau, Xavier Marat, Jean-Pierre Vors, David Virieux and Jean-Luc Pirat

Affiliation:

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

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.

Cite this article as:

Cristau Henri-Jean, Marat Xavier, Vors Jean-Pierre, Virieux David and Pirat Jean-Luc, Synthesis of α,α-Disubstituted α-Acetoxy Esters and α,α-Disubstituted α- Hydroxy Acids by Baeyer-Villiger Oxidation of the Corresponding β- Ketoesters, Current Organic Synthesis 2005; 2 (1) . https://dx.doi.org/10.2174/1570179052996928