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 CF 3-modified dipeptides carrying two different N-protecting groups. These peptidomimetic units are characterized by the presence of the [CH(CF 3)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. © 2014 Springer-Verlag.

Trifluoromethyl-modified dipeptides by ZrCl4-promoted aza-Henry reactions / Fioravanti, Stefania; Pelagalli, Alessia; Pellacani, Lucio; Sciubba, Fabio; Vergari, MARIA CECILIA. - In: AMINO ACIDS. - ISSN 0939-4451. - STAMPA. - 46:8(2014), pp. 1961-1970. [10.1007/s00726-014-1749-4]

Trifluoromethyl-modified dipeptides by ZrCl4-promoted aza-Henry reactions

FIORAVANTI, Stefania;PELAGALLI, ALESSIA;PELLACANI, Lucio;SCIUBBA, FABIO;VERGARI, MARIA CECILIA
2014

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 CF 3-modified dipeptides carrying two different N-protecting groups. These peptidomimetic units are characterized by the presence of the [CH(CF 3)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. © 2014 Springer-Verlag.
2014
amino acids; nmr techniques; organo-fluorine chemistry; peptidomimetics
01 Pubblicazione su rivista::01a Articolo in rivista
Trifluoromethyl-modified dipeptides by ZrCl4-promoted aza-Henry reactions / Fioravanti, Stefania; Pelagalli, Alessia; Pellacani, Lucio; Sciubba, Fabio; Vergari, MARIA CECILIA. - In: AMINO ACIDS. - ISSN 0939-4451. - STAMPA. - 46:8(2014), pp. 1961-1970. [10.1007/s00726-014-1749-4]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/557649
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