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Updated: May 26, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Regioselective base-free intermolecular aminohydroxylations of hindered and functionalized alkenes
Zhiwei Ma1, Bradley C Naylor, Brad M Loertscher
1Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, USA.
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.
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