A practical synthesis of enantiopure syn-β-amino-α-hydroxy acids from α-amino acids with application in the formal syntheses of l-TFB-TBOA and (S)-vigabatrin

Abstract

Enantiopure syn-β-amino-α-hydroxy acids have been synthesized from α-amino acids in a multi-step procedure that exhibits a high level of stereoselectivity and good overall yields. A stepwise oxidation of the terminal olefin to a carboxylic acid delivered an essentially quantitative yield via a cleaner process relative to the conventional one-pot oxidation. The practical value of this transformation has been demonstrated in the formal synthesis of L-TFB-TBOA and (S)-vigabatrin.