Asymmetric Access to α-Substituted Functional Aspartic Acid Derivatives by a [3+2] Strategy Employing a Chiral Dienophile

Kawther Ben Ayed (1) , Anne Beauchard (1) , Jean-François Poisson (2) , Sandrine Py (2) , Mathieu Y. Laurent (1) , Arnaud Martel (1) , Houcine Ammar (3) , Souhir Abid (3) , Gilles Dujardin (1)

1 IMMM - Institut des Molécules et Matériaux du Mans
2 DCM - SeRCO - Département de Chimie Moléculaire - Synthèse Et Réactivité en Chimie Organique
3 Université de Sfax - University of Sfax

Enantiopure vinyl ethers of Stericol® underwent diastereoselective thermal 1,3 dipolar cycloadditions with N-benzyl, N-benzhydryl, and N-PMB aspartate ester nitrones. Chemoselective N-debenzylation of the resulting cycloadducts afforded diastereomerically and enantiomerically pure crystalline NH-isoxazolidine, the absolute configuration of which was established by X-ray crystallography. N-Protection and N–O cleavage of this isoxazolidine gave enantioenriched quaternary aspartate derivatives bearing functionalized side chains.

Mots clés: Asymmetric synthesis; Cycloaddition; Amino acids; Heterocycles

Domaines: Chimie

Kawther Ben Ayed, Anne Beauchard, Jean-François Poisson, Sandrine Py, Mathieu Y. Laurent, et al.. Asymmetric Access to α-Substituted Functional Aspartic Acid Derivatives by a [3+2] Strategy Employing a Chiral Dienophile. European Journal of Organic Chemistry, 2014, 2014 (14), pp.2924-2932. ⟨10.1002/ejoc.201301739⟩. ⟨hal-01652161⟩