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
Revue
Eur. J. Org. Chem.
Volume
2014
Pagination
2924–2932
ISSN
1099-0690
Soumis le 12 avril 2018