Asymmetric access to peptidyl beta-aldehydes by coupling of N-phthalyl alpha-amino acids with a synthetic heterocyclic beta-amino aldehyde precursor

Biaolin Yin (1) , Robert Dhal (1) , Vincent Maisonneuve (2) , Gilles Dujardin (1)

1 UCO2M - Unité de chimie organique moléculaire et macromoléculaire
2 LdOF - Laboratoire des oxydes et fluorures

Asymmetric access to novel N-protected (di)peptidyl β3-aldehydes (“β3-PAs”) has been achieved through direct coupling of a chiral non-racemic 6-alkoxytetrahydrooxazinone with N-phthalyl L-α-amino acids. Kinetic resolution allows for the fruitful use of racemic amino acids in this process. Acidic hydrolysis of the diastereomerically pure, coupling products leads to the title N-phthalyl-β3-PAs in high yields.

Mots clés: β-Peptide aldehydes; Coupling reactions; Tetrahydrooxazinones; Kinetic resolution

Domaines: Chimie organique

Biaolin Yin, Robert Dhal, Vincent Maisonneuve, Gilles Dujardin. Asymmetric access to peptidyl beta-aldehydes by coupling of N-phthalyl alpha-amino acids with a synthetic heterocyclic beta-amino aldehyde precursor. European Journal of Organic Chemistry, 2006, 15, pp.3309-3313. ⟨10.1002/ejoc.200600262⟩. ⟨hal-00110632⟩