Improved enzymatic syntheses of valuable β-arylalkyl-β-amino acid enantiomers

Abstract

The enantioselective (E∼ 200) Burkholderia cepacia-catalysed hydrolyses of β-amino esters with H₂O (0.5 equiv.) in t-BuOMe or in i-Pr₂O at 45 °C are described. The enantiomers of biologically relevant β-arylalkyl-substituted β-amino acids, and especially (R)-3-amino-3-(2,4,5-trifluorophenyl)butanoic acid, the intermediate of the new antidiabetic drug sitagliptine, were prepared with high enantiomeric excesses (ee≥96%) and in good yields (≥42%).