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

Abstract

Abstract 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%).