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

作者：Shpak Kraievskyi Pavlo; Yin Biaolin; Martel Arnaud; Dhal Robert; Dujardin Gilles; Laurent Mathieu Y^*

来源：Tetrahedron, 2012, 68(9): 2179-2188.

DOI：10.1016/j.tet.2012.01.002

• Transacetalization
• Peptide aldehyde
• beta-Amino acetal
• Maraviroc
• Peptide coupling

Efficient access to masked beta-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.

• 出版日期2012-3-4