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

Files in This Item:
File Description SizeFormat 
O'Reilly Amino Acids 2010.doc354 kBMicrosoft WordDownload
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
Copyright (published version): 2010 Springer
Keywords: (S)-Deuterated-alpha-amino acids;diketopiperazine;Asymmetric 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

Show full item record

SCOPUSTM   
Citations 50

2
Last Week
0
Last month
checked on Jun 22, 2018

Page view(s) 10

181
checked on May 25, 2018

Download(s) 50

163
checked on May 25, 2018

Google ScholarTM

Check

Altmetric


This item is available under the Attribution-NonCommercial-NoDerivs 3.0 Ireland. No item may be reproduced for commercial purposes. For other possible restrictions on use please refer to the publisher's URL where this is made available, or to notes contained in the item itself. Other terms may apply.