title: Regioselective base-free intermolecular aminohydroxylations of hindered and functionalized alkenes.
abstract: Regioselective base-free intermolecular aminohydroxylations of functionalized trisubstituted and 1,1-disubstituted alkenes employing benzoyloxycarbamate 3a and catalytic OsO(4) are described. In all cases, the more substituted alcohol isomer is favored. Sluggish reactions could be promoted by gentle heating, the use of amine ligands, or increased catalyst loadings. A competitive rearrangement was observed with a secondary allylic alcohol substrate. The adducts serve as useful precursors to dehydroamino acids.
authors.affiliation: Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, USA.
authors.forename: Zhiwei
authors.initials: Z
authors.lastname: Ma
authors.forename: Bradley C
authors.initials: BC
authors.lastname: Naylor
authors.forename: Brad M
authors.initials: BM
authors.lastname: Loertscher
authors.forename: Danny D
authors.initials: DD
authors.lastname: Hafen
authors.forename: Jasmine M
authors.initials: JM
authors.lastname: Li
authors.forename: Steven L
authors.initials: SL
authors.lastname: Castle
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000588:Amines; D000605:Amino Alcohols; D008024:Ligands