Access to C-protected β-amino-aldehydes via transacetalization of 6-alcoxy tetrahydrooxazinones and use for pseudo-peptide synthesis

Pavlo Shpak-Kraievskyi (1) , Biaolin Yin (1) , Arnaud Martel (1) , Robert Dhal (1) , Gilles Dujardin (1) , Mathieu Y. Laurent (1)

1 UCO2M - Unité de chimie organique moléculaire et macromoléculaire

Efficient access to masked β-amino-aldehydes was performed starting from 6-alcoxy tetrahydrooxazinone 6a–d (6-ATO). Transacetalization leads to the opening of the cycle to form either unsymmetric acetal 7 or symmetric acetals 16–18. These amino acetals are key compounds, obtained with 99% ee, which can be engaged in efficient peptide coupling. This method could easily provide peptides aldehydes or small amido aldehydes as exemplified with the formal synthesis of ent-Maraviroc.

Mots clés: Peptide coupling; Transacetalization; peptide aldehyde; β-amino acetal; Maraviroc

Domaines: Chimie organique

Pavlo Shpak-Kraievskyi, Biaolin Yin, Arnaud Martel, Robert Dhal, Gilles Dujardin, et al.. Access to C-protected β-amino-aldehydes via transacetalization of 6-alcoxy tetrahydrooxazinones and use for pseudo-peptide synthesis. Tetrahedron, 2012, 68 (9), pp.2179-2188. ⟨10.1016/j.tet.2012.01.002⟩. ⟨hal-00700165⟩