A stereoselective synthesis of α-deuterium-labelled (S)-α-amino acids
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- O’Reilly, E., Balducci, D. & Paradisi, F. Amino Acids (2010) 39: 849. doi:10.1007/s00726-010-0541-3
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An atom-efficient and stereoselective synthesis has been developed for the preparation of α-2H-labelled (S)-α-amino acids, starting from a novel chiral diketopiperazine scaffold. Efficient mono-alkylation of the chiral template afforded the (S)-substituted adducts with the nature of the electrophile significantly effecting the stereochemical outcome. Subsequent alkylation was totally selective producing the 1,4-cis adduct as the sole diastereoisomer. The deprotection was carried out using cerium ammonium nitrate followed by acid hydrolysis affording the enantipure α-amino acids.