Now showing 1 - 1 of 1
No Thumbnail Available

A stereoselective synthesis of α-deuterium labelled (S)-α-amino acids

2010, O'Reilly, Elaine, Balducci, Daniele, Paradisi, Francesca

An atom-efficient and stereoselective synthesis has been developed for the preparation of a-2H-labelled(S)-a-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 a-amino acids.