Publication detail

Design and Synthesis of Optically Active 2-Phenylimidazolecarboxamides Featuring Amino Acid Motive

Authors: Sívek Roman | Pytela Oldřich | Bureš Filip

Year: 2008

Type of publication: článek v odborném periodiku

Name of source: Journal of Heterocyclic Chemistry

Publisher name: Wiley-Blackwell

Page from-to: 1621-1627

Titles:

Language	Name	Abstract	Keywords
cze	Design a syntéza opticky aktivních 2-fenylimidazolkarboxamidů na bázi amino kyselin	Celkem bylo syntetizováno šestnáct nových, opticky aktivních karboxamidů na bázi 2-fenylimidazolu a amino kyselin s využitím dvou reakčních cest. První metoda zahrnuje reakci acylchloridů, druhá využívá reakci směsných anhydridů s příslušnou amino kyselinou. Předběžné testy připravených carboxamidů v Henryho či aldolové reakci poskytly pouze nízké ee.	imidazol; karboxamidy, nitroaldolová kondenzace
eng	Design and Synthesis of Optically Active 2-Phenylimidazolecarboxamides Featuring Amino Acid Motive	Overall sixteen new, optically active carboxamides 1-3 have been synthesized. These compounds based on the 2-phenylimidazole and featuring amino acid residues are linked on the 4-position by an amidicbond. Two general methods were used for their construction. Whereas the first method employs acylchlorides as a reactive species, the second one involves a condensation of mixed anhydrides with the amino acid counterparts. Actually, the second method proved to be more efficient than the first one. Carboxamides 1-3 were preliminarily tested as N-chelating ligands with an application in the Henry or Aldol reactions affording either poor yields or enantiomeric excesses.	imdiazole; carboxamides; nitroaldol reaction

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