A new and concise strategy to the enantioselective synthesis of (S)-2-amino-4-oxo-4-(pyridine-2-yl) butanoic acid from aspartic acid

The a-amino acid (S)-5 was synthesized using in the key step a chemoselective nucleophilic substitution between a diester derived from L-aspartic acid and 2-lithium pyridine. The overall yield (13%, 5 steps) was similar to those previously described by our group for the R isomer (the first exogen fu...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the Brazilian Chemical Society 2010, Vol.21 (5), p.777-781
Main Authors: Lima, Evanoel Crizanto de, Lima, Paulo G. de, Souza, Carolina C. de, Maior, Marta C. L. S., Dias, Ayres G., Costa, Paulo R. R.
Format: Article
Language:English
Subjects:
CHEMISTRY, MULTIDISCIPLINARY
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The a-amino acid (S)-5 was synthesized using in the key step a chemoselective nucleophilic substitution between a diester derived from L-aspartic acid and 2-lithium pyridine. The overall yield (13%, 5 steps) was similar to those previously described by our group for the R isomer (the first exogen full agonist of the NMDA receptors) from D-mannitol (12%, 10 steps) and by Lovey and Copper for the racemic synthesis (17%, 5 steps).
ISSN:0103-5053
1678-4790
DOI:10.1590/S0103-50532010000500002