Totally diastereoselective addition of aryl Grignard reagents to the nitrone-based chiral glycine equivalent MiPNO.

Maryse Thiverny (1) , Daniel Farran (2) , Christian Philouze (2) , Véronique Blandin (1) , Pierre Yves Chavant (1)

1 DCM - SeRCO - Département de Chimie Moléculaire - Synthèse Et Réactivité en Chimie Organique
2 DCM - Département de Chimie Moléculaire

The reaction of the chiral nitrone MiPNO (2-isopropyl-2,3-dimethyl-1-oxy-2,3-dihydro-imidazol-4-one) with Grignard reagents is totally diastereoselective. Using simple and functionalized arylmagnesium reagents, enantiopure hydroxylamines were obtained in fair to good yields, which in turn could be easily transformed into new chiral ketonitrones. The prepn. of enantiopure L-phenylglycine derivs. is also described. [on SciFinder(R)]

Domaines: Chimie organique

Maryse Thiverny, Daniel Farran, Christian Philouze, Véronique Blandin, Pierre Yves Chavant. Totally diastereoselective addition of aryl Grignard reagents to the nitrone-based chiral glycine equivalent MiPNO.. Tetrahedron: Asymmetry, 2011, 22 (12), pp.1274-1281. ⟨10.1016/j.tetasy.2011.07.022⟩. ⟨hal-00638243⟩