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Synthesis of Optically Active α-Hydroxy Acids by Kinetic Resolution Through Lipase-Catalyzed Enantioselective Acetylation

1998; Wiley; Volume: 1998; Issue: 9 Linguagem: Inglês

10.1002/(sici)1099-0690(199809)1998

1434-193X

Waldemar Adam, Michael Lazarus, Alexandra Schmerder, Hans‐Ulrich Humpf, Chantu R. Saha‐Möller, Peter Schreier,

Chemical synthesis and alkaloids

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.