title: Synthesis of virtually enantiopure aminodiols with three adjacent stereogenic centers by epoxidation and ring-opening.
abstract: A virtually complete enantioselective synthesis of 3-amino-1,2-diols with three consecutive stereocenters was accomplished by a sequential cascade of two kinetic resolutions, which features a Sharpless or Hafnium-catalyzed asymmetric epoxidation and a subsequent W-catalyzed aminolysis. Enantiopure products with up to >99.9% ee and >99.9 : 0.1 dr were obtained and could serve as potential building blocks for pharmaceutical or biological significant molecules.
authors.affiliation: Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
authors.forename: Lan
authors.initials: L
authors.lastname: Luo
authors.forename: Hisashi
authors.initials: H
authors.lastname: Yamamoto
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D004852:Epoxy Compounds / Q000737:chemistry*; D006195:Hafnium / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry; D014414:Tungsten / Q000737:chemistry
chemical_list: D000438:Alcohols; D000588:Amines; D004852:Epoxy Compounds; D014025:Titanium; D014414:Tungsten; D006195:Hafnium