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

Author(s)
O'Reilly, Elaine  
Balducci, Daniele  
Paradisi, Francesca  
Uri
http://hdl.handle.net/10197/3640
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.
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
Subjects

(S)-Deuterated-alpha-...

diketopiperazine

Asymmetric synthesis

Subject – LCSH
Amino acids--Synthesis
Organic cyclic compounds
Asymmetric synthesis
DOI
10.1007/s00726-010-0541-3
Language
English
Status of Item
Peer reviewed
This item is made available under a Creative Commons License
https://creativecommons.org/licenses/by-nc-sa/1.0/
File(s)
No Thumbnail Available
Name

O'Reilly Amino Acids 2010.doc

Size

354 KB

Format

Microsoft Word

Checksum (MD5)

f3ca75cc5f583778d456d687d7045a62

Owning collection
Chemistry Research Collection

Item descriptive metadata is released under a CC-0 (public domain) license: https://creativecommons.org/public-domain/cc0/.
All other content is subject to copyright.

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