Asymmetric access to α-substituted functional aspartic acid derivatives by a [3+2] strategy employing a chiral dienophile.
Enantiopure vinyl ethers of Stericol underwent diastereoselective thermal 1,3 dipolar cycloaddns. with N-benzyl, N-benzhydryl, and N-PMB aspartate ester nitrones. Chemoselective N-debenzylation of the resulting cycloadducts afforded diastereomerically and enantiomerically pure cryst. NH-isoxazolidine, the abs. configuration of which was established by X-ray crystallog. N-Protection and N-O cleavage of this isoxazolidine gave enantioenriched quaternary aspartate derivs. bearing functionalized side chains.
Références
- Titre
- Asymmetric access to α-substituted functional aspartic acid derivatives by a [3+2] strategy employing a chiral dienophile.
- Type de publication
- Article de revue
- Année de publication
- 2014
- Auteurs
- Ben Ayed, Kawther, Beauchard Anne, Poisson Jean-François, Py Sandrine, Laurent Mathieu Y., Martel Arnaud, Ammar Houcine, Abid Souhir, and Dujardin Gilles.
- Revue
- Eur. J. Org. Chem.
- Volume
- 2014
- Pagination
- 2924–2932
- ISSN
- 1099-0690
Soumis le 12 avril 2018