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.