A stereoselective synthesis of alpha-deuterium-labelled (S)-alpha-amino acids.
An atom-efficient and stereoselective synthesis has been developed for the preparation of alpha-2H-labelled (S)-alpha-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 alpha-amino acids.
O'Reilly
Elaine
E
UCD School of Chemistry and Chemical Biology, Centre for Synthesis and Chemical Biology, Belfield, Dublin 4, Ireland.
Balducci
Daniele
D
Paradisi
Francesca
F
D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D003903:Deuterium / Q000737:chemistry*; D054659:Diketopiperazines / Q000737:chemistry; D006868:Hydrolysis; D007553:Isotope Labeling; D013237:Stereoisomerism
D000596:Amino Acids; D054659:Diketopiperazines; D003903:Deuterium