Design and synthesis of optically active 2-phenylimidazolecarboxamides featuring amino acid motive

✍ Scribed by Roman Sivek; Oldřich Pytela; Filip Bureš

• Book ID: 102342339
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2008
• Tongue: English
• Weight: 258 KB
• Volume: 45
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570450611

✦ Synopsis

Abstract

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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 amidic bond. 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.