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Regioselective Base-Free Intermolecular Aminohydroxylations of Hindered and Functionalized Alkenes
journal contribution
posted on 2012-01-20, 00:00 authored by Zhiwei Ma, Bradley C. Naylor, Brad M. Loertscher, Danny
D. Hafen, Jasmine M. Li, Steven L. CastleRegioselective base-free intermolecular aminohydroxylations
of
functionalized trisubstituted and 1,1-disubstituted alkenes employing
benzoyloxycarbamate 3a and catalytic OsO4 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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allylic alcohol substrateadductdehydroamino acidsRegioselectivedisubstitutedbenzoyloxycarbamate 3OsO 4catalyst loadingsAminohydroxylationSluggish reactionsalkenealcohol isomeraminohydroxylationAlkenesRegioselectiveFunctionalizedprecursorHinderedamine ligandsheatingrearrangementfunctionalized trisubstitutedIntermolecular
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