Amino Acids

, Volume 39, Issue 3, pp 849–858

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

Original Article

DOI: 10.1007/s00726-010-0541-3

Cite this article as:
O’Reilly, E., Balducci, D. & Paradisi, F. Amino Acids (2010) 39: 849. doi:10.1007/s00726-010-0541-3

Abstract

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.

Keywords

(S)-Deuterated-α-amino acidsDiketopiperazineAsymmetric synthesis

Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  1. 1.UCD School of Chemistry and Chemical BiologyCentre for Synthesis and Chemical BiologyDublin 4Ireland