N-Heteroarylation of chiral α-aminoesters by means of palladium-catalyzed Buchwald-Hartwig reaction.
J Org Chem
; 78(16): 7930-7, 2013 Aug 16.
Article
em En
| MEDLINE
| ID: mdl-23844999
ABSTRACT
N-Heteroaryl-α-amino acid derivatives are valuable pharmacological agents as peptidomimetics. Classical SNAr methods using acid catalysis and elevated temperatures could not be extended to various α-amino acids and fairly electrophilic heterocyclic partners. Here, we report a mild and versatile method of N-heteroarylation of chiral α-aminoesters without racemization, involving Buchwald-Hartwig conditions. It could be extended to various α-amino acids and azines. This efficient N-heteroarylation leads to (i) a chemical library of putative peptidomimetics combining diverse azaheterocycles with the chiral α-aminoesters and their corresponding derivatives (amides, alcohols, etc.) and (ii) arginine derivatives designed as NPFF receptor ligands.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Paládio
/
Ésteres
/
Aminoácidos
Idioma:
En
Ano de publicação:
2013
Tipo de documento:
Article