Synthèses Asymétriques et Synthèses Asymétriques Potentielles D'α-Amino Alcools: Hydroxyamination D'Oléfines par la Méthode de Sharpless

Optically active α-amino alcohols have been synthesized by Sharpless method with (-)-10,11-dihydroquinine 2 and (R) - (-)-pantolactone 8 as chiral inducers. Five secondary (dl)alcohols: 3,4,5,6,7 and (dl) 2-hydroxyheptahelicene 1 have also been used to prepare the intermediate diastereomeric (dl)α-hydroxy carbamates 9. The highest inductions were obtained with (-)-10,11-dihydroquinine and (E)-stilbene (e.e. ≥98%) and with (dl)2-hydroxyheptahelicene and (E)-stilbene (d.e. ≥98%).