Stereoselective synthesis of short benzyl malonyl peptides

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.

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

Fioravanti

Pelagalli

Pellacani

et al. 2014

Amino Acids

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Straightforward synthesis of biologically valuable nonsymmetrical malonamides under mild conditions

et al. 2022

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Stereoselective synthesis of short benzyl malonyl peptides

Abstract: A Rh-catalyzed addition reaction on non symmetric dehydro alanine retro-peptides is the key step in the reported three-step strategy for the diastereoselective synthesis of differently functionalized benzyl malonyl peptides (74% overall yield)

Cited by 2 publications

References 28 publications

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

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

Straightforward synthesis of biologically valuable nonsymmetrical malonamides under mild conditions

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