10.1021/jo202375a.s001 Zhiwei Ma Zhiwei Ma Bradley C. Naylor Bradley C. Naylor Brad M. Loertscher Brad M. Loertscher Danny D. Hafen Danny D. Hafen Jasmine M. Li Jasmine M. Li Steven L. Castle Steven L. Castle Regioselective Base-Free Intermolecular Aminohydroxylations of Hindered and Functionalized Alkenes American Chemical Society 2012 allylic alcohol substrate adduct dehydroamino acids Regioselective disubstituted benzoyloxycarbamate 3 OsO 4 catalyst loadings Aminohydroxylation Sluggish reactions alkene alcohol isomer aminohydroxylation AlkenesRegioselective Functionalized precursor Hindered amine ligands heating rearrangement functionalized trisubstituted Intermolecular 2012-01-20 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Regioselective_Base_Free_Intermolecular_Aminohydroxylations_of_Hindered_and_Functionalized_Alkenes/2557561 Regioselective base-free intermolecular aminohydroxylations of functionalized trisubstituted and 1,1-disubstituted alkenes employing benzoyloxycarbamate <b>3a</b> and catalytic OsO<sub>4</sub> 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.