Scandium-bipyridine-catalyzed enantioselective aminolysis of meso-epoxides.
The scandium-bipyridine-catalyzed enantioselective addition of anilines and O-alkyl hydroxylamines to meso-epoxides has been optimized and extended to a broad range of epoxides and amines. Whereas aromatic meso-epoxides generally furnished the corresponding 1,2-amino alcohols in excellent enantioselectivities, aliphatic meso-epoxides only gave rise to moderate enantioselectivities in the aminolysis. The catalyst loading may be lowered to just 5 mol% with only marginal effects on yield and enantioselectivity. A strong positive nonlinear effect has been observed, pointing to aggregation phenomena of the catalyst.
Mai
Enzo
E
Institut für Organische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany.
Schneider
Christoph
C
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D004852:Epoxy Compounds; D011725:Pyridines; C023666:pyridine; D012538:Scandium