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A stereoselective synthesis of α-deuterium labelled (S)-α-amino acids
Date Issued
2010
Date Available
2012-06-13T15:39:44Z
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.
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.
Sponsorship
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
Subject – LCSH
Amino acids--Synthesis
Organic cyclic compounds
Asymmetric synthesis
Language
English
Status of Item
Peer reviewed
This item is made available under a Creative Commons License
File(s)
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Name
O'Reilly Amino Acids 2010.doc
Size
354 KB
Format
Microsoft Word
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