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

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dc.contributor.author O'Reilly, Elaine
dc.contributor.author Balducci, Daniele
dc.contributor.author Paradisi, Francesca
dc.date.accessioned 2012-06-13T15:39:44Z
dc.date.available 2012-06-13T15:39:44Z
dc.date.copyright 2010 Springer en
dc.date.issued 2010
dc.identifier.citation Amino Acids en
dc.identifier.uri http://hdl.handle.net/10197/3640
dc.description.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. en
dc.description.sponsorship Higher Education Authority en
dc.description.sponsorship Irish Research Council for Science, Engineering and Technology en
dc.format.extent 362496 bytes
dc.format.mimetype application/msword
dc.language.iso en en
dc.publisher Springer en
dc.rights The final publication is available at springerlink.com en
dc.subject (S)-Deuterated-alpha-amino acids en
dc.subject diketopiperazine en
dc.subject Asymmetric synthesis en
dc.subject.lcsh Amino acids--Synthesis en
dc.subject.lcsh Organic cyclic compounds en
dc.subject.lcsh Asymmetric synthesis en
dc.title A stereoselective synthesis of α-deuterium labelled (S)-α-amino acids en
dc.type Journal Article en
dc.internal.availability Full text available en
dc.status Peer reviewed en
dc.identifier.volume 39 en
dc.identifier.issue 3 en
dc.identifier.startpage 849 en
dc.identifier.endpage 858 en
dc.identifier.doi 10.1007/s00726-010-0541-3
dc.neeo.contributor O'Reilly|Elaine|aut| en
dc.neeo.contributor Balducci|Daniele|aut| en
dc.neeo.contributor Paradisi|Francesca|aut| en

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