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Keywords:

  • amino alcohols;
  • aminolysis;
  • asymmetric catalysis;
  • epoxides;
  • scandium bipyridine

Abstract

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.