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

Organic & Biomolecular Chemistry Pub Date: 2009-12-17 DOI: 10.1039/B920731G

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%).

Graphical abstract: Improved enzymatic syntheses of valuable β-arylalkyl-β-amino acid enantiomers
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