The lipase‐catalyzed acetylation of a broad spectrum of racemic 2‐hydroxy acids 1 to their 2‐acetoxy acids 2 was shown to proceed with high enantioselectivity. Thus, the microbial lipases, in particular from Candidaantarctica and Burkholderiaspecies, are convenient biocatalysts for the synthesis of optically active 2‐hydroxy acids in excellent enantioselectivity (ee values up to > 99%). The absolute configurations of the 2‐hydroxy acids 1 were assigned by comparison of the gas‐chromatographic data with that of literature‐known reference compounds, or by means of the exciton‐coupled circular dichroism method (ECCD) on their bichromophoric 2‐naphthoate 9‐anthrylmethyl derivatives 3. These results establish that (S)‐2‐hydroxy acids 1 were preferentially acetylated by microbial lipases.
hydroxycarboxylic acidshydroxycarboxylic acids (ether carboxylic acids) (acyclic compounds) and esters P 0280
-062Synthesis of Optically Active α-Hydroxy Acids by Kinetic Resolution Through Lipase-Catalyzed Enantioselective Acetylation.-Lipases from Candida antarctica and from Burkholderia species are found to be efficient and convenient bio-catalysts for the synthesis of optically active α-hydroxy acids via enantioselective acetylation. The yields of the title compounds range from 76 to 91% based on conversion. Absolute configurations are determined by exciton-coupled circular dichroism.-(ADAM, W.; LAZARUS, M.; SCHMERDER, A.; HUMPF, H.-U.; SAHA-MOELLER, C. R.; SCHREIER, P.; Eur.
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