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

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

Journal Name: Current Organic Synthesis

Volume 2 , Issue 1 , 2005

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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

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Article Details

Year: 2005
Page: [113 - 119]
Pages: 7
DOI: 10.2174/1570179052996928

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PDF: 66