title: Aminodiols via stereocontrolled oxidation of methyleneaziridines.
abstract: A highly diastereoselective Ru-catalyzed oxidation/reduction sequence of bicyclic methyleneaziridines provides a facile route to complex 1-amino-2,3-diol motifs. The relative anti stereochemistry between the amine and the vicinal alcohol are proposed to result from 1,3-bischelation in the transition state by the C1 and C3 heteroatoms.
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison , Madison Wisconsin 53706, United States.
authors.forename: Jared W
authors.initials: JW
authors.lastname: Rigoli
authors.forename: Ilia A
authors.initials: IA
authors.lastname: Guzei
authors.forename: Jennifer M
authors.initials: JM
authors.lastname: Schomaker
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D001388:Aziridines; D002219:Carbamates; D012428:Ruthenium