title: Osmium-catalyzed tethered aminohydroxylation of glycals: a stereodirected access to 2- and 3-aminosugars.
abstract: The osmium-catalyzed aminohydroxylation of glycals has been achieved with complete regio- and stereocontrol by taking advantage of the Donohoe tethering approach. Glucals and galactals showed complementary reactivity in dependence of the stage at which the reaction was performed, i.e., directly or after double-bond shift consequent to a Ferrier rearrangement (that is, on the 1,2 or 2,3-unsaturated sugar), allowing access to both classes of 2-amino (mannosamine) and 3-amino (talosamine) sugar derivatives, respectively.
authors.affiliation: Dipartimento di Chimica "Ugo Schiff", Università di Firenze , Via della Lastruccia 3-13, I-50019 Sesto Fiorentino (FI), Italy , associated with ICCOM-CNR, Firenze, Italy.
authors.forename: Stefania
authors.initials: S
authors.lastname: Mirabella
authors.forename: Francesca
authors.initials: F
authors.lastname: Cardona
authors.forename: Andrea
authors.initials: A
authors.lastname: Goti
mesh_terms: D000606:Amino Sugars / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry; D002384:Catalysis; D005697:Galactosides / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006595:Hexosamines / Q000138:chemical synthesis* / Q000737:chemistry; D006900:Hydroxylation; D015394:Molecular Structure; D009992:Osmium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000606:Amino Sugars; D002241:Carbohydrates; D005697:Galactosides; D006027:Glycosides; D006595:Hexosamines; C000596577:talosamine; C008322:mannosamine; D009992:Osmium