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

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Title: A stereoselective synthesis of α-deuterium labelled (S)-α-amino acids
Authors: O'Reilly, Elaine
Balducci, Daniele
Paradisi, Francesca
Permanent link: http://hdl.handle.net/10197/3640
Date: 2010
Abstract: 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.
Funding Details: Higher Education Authority
Irish Research Council for Science, Engineering and Technology
Type of material: Journal Article
Publisher: Springer
Journal: Amino Acids
Volume: 39
Issue: 3
Start page: 849
End page: 858
Copyright (published version): 2010 Springer
Keywords: (S)-Deuterated-alpha-amino acidsdiketopiperazineAsymmetric synthesis
Subject LCSH: Amino acids--Synthesis
Organic cyclic compounds
Asymmetric synthesis
DOI: 10.1007/s00726-010-0541-3
Language: en
Status of Item: Peer reviewed
Appears in Collections:Chemistry Research Collection

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