O'Reilly, ElaineElaineO'ReillyBalducci, DanieleDanieleBalducciParadisi, FrancescaFrancescaParadisi2012-06-132012-06-132010 Sprin2010Amino Acidshttp://hdl.handle.net/10197/3640An 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.362496 bytesapplication/mswordenThe final publication is available at springerlink.com(S)-Deuterated-alpha-amino acidsdiketopiperazineAsymmetric synthesisAmino acids--SynthesisOrganic cyclic compoundsAsymmetric synthesisJournal Article39384985810.1007/s00726-010-0541-3https://creativecommons.org/licenses/by-nc-sa/1.0/