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

Organic & Biomolecular Chemistry
Gábor TasnádiFerenc Fülöp

Abstract

The enantioselective (E approximately 200) Burkholderia cepacia-catalysed hydrolyses of beta-amino esters with H(2)O (0.5 equiv.) in t-BuOMe or in i-Pr(2)O at 45 degrees C are described. The enantiomers of biologically relevant beta-arylalkyl-substituted beta-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>or=96%) and in good yields (>or=42%).

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Citations

Jul 27, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Eniko ForróFerenc Fülöp
Dec 23, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sayeh ShahmohammadiEnikő Forró

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