title: Trifluoromethyl-modified dipeptides by ZrCl4-promoted aza-Henry reactions.
abstract: Chiral (R)-1-phenylethylamine was successfully employed in a tandem aza-Henry addition-reduction reaction to give chiral β-nitro α-trifluoromethyl amines. A subsequent coupling reaction with N-Boc-protected amino acids leads to obtain optically pure CF3-modified dipeptides carrying two different N-protecting groups. These peptidomimetic units are characterized by the presence of the [CH(CF3)NH] group as mimetic of the natural [CONH] peptidic bond and can be used for the synthesis of more complex CF3-modified peptides after selective deprotection of one of the two amine functions. 2D NMR spectral analyses were employed to determine the absolute configurations of all newly synthesized chiral compounds.
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Roma "La Sapienza", P.le Aldo Moro 5, 00185, Rome, Italy, stefania.fioravanti@uniroma1.it.
authors.forename: Stefania
authors.initials: S
authors.lastname: Fioravanti
authors.forename: Alessia
authors.initials: A
authors.lastname: Pelagalli
authors.forename: Lucio
authors.initials: L
authors.lastname: Pellacani
authors.forename: Fabio
authors.initials: F
authors.lastname: Sciubba
authors.forename: Maria Cecilia
authors.initials: MC
authors.lastname: Vergari
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry*; D004151:Dipeptides / Q000378:metabolism*; D005461:Fluorine / Q000737:chemistry; D017611:Fluorine Compounds / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D010627:Phenethylamines / Q000737:chemistry*; D015040:Zirconium / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D002712:Chlorides; D004151:Dipeptides; D017611:Fluorine Compounds; D010627:Phenethylamines; D005461:Fluorine; D015040:Zirconium; C429984:zirconium chloride