Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5220883 | Tetrahedron | 2012 | 10 Pages |
Abstract
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.
Graphical abstractDownload full-size image
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Pavlo Shpak-Kraievskyi, Biaolin Yin, Arnaud Martel, Robert Dhal, Gilles Dujardin, Mathieu Y. Laurent,