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A titanium tetrachloride-based effective methodology for the synthesis of dipeptides.

ABSTRACT: A series of dipeptide systems have been easily achieved through a TiCl₄-assisted condensation reaction. The reaction of N-protected amino acids with amino acid methyl esters in pyridine and in the presence of TiCl₄ furnished the corresponding dipeptides with high yields and diastereoselectivity. The reaction was successfully applied to amino acids protected on the α-amino function with different protecting groups. The adopted experimental conditions allowed preserving both the protecting groups on the α-amino function and on the side chain functionalities. Furthermore, the preservation of the stereochemical integrity at the amino acid chiral centres has been verified.

SUBMITTER: Comande A

PROVIDER: S-EPMC9066614 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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A titanium tetrachloride-based effective methodology for the synthesis of dipeptides.

Comandè Alessandra A Greco Marianna M Belsito Emilia Lucia EL Liguori Angelo A Leggio Antonella A

RSC advances 20190717 38

A series of dipeptide systems have been easily achieved through a TiCl<sub>4</sub>-assisted condensation reaction. The reaction of N-protected amino acids with amino acid methyl esters in pyridine and in the presence of TiCl<sub>4</sub> furnished the corresponding dipeptides with high yields and diastereoselectivity. The reaction was successfully applied to amino acids protected on the α-amino function with different protecting groups. The adopted experimental conditions allowed preserving both ...[more]

PMID: 35518841

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