Abstract
By using (N-tosyloxy)-3-O-carbamoyl-D-glucal 10, which removes the need for a hypervalent iodine(III) oxidant, we provide evidence for rhodium nitrenoid-mediated ipso C-H activation as the origin of a C3-oxidized dihydropyranone product 3. This system may be especially susceptible to such a pathway because of the ease of forming a cation upon hydride transfer to the rhodium-complexed acyl nitrene.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Calcium Gluconate / chemistry*
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Carbamates / chemistry*
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Carbonates / chemistry
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Catalysis
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Hydrogen Bonding
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Kinetics
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Molecular Structure
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Organometallic Compounds / chemistry*
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Oxidants / chemistry*
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Potassium / chemistry
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Rhodium / chemistry*
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Tosyl Compounds / chemistry*
Substances
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(N-tosyloxy)-3-O-carbamoyl-D-glucal
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Carbamates
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Carbonates
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Organometallic Compounds
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Oxidants
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Tosyl Compounds
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potassium carbonate
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Rhodium
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Potassium
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Calcium Gluconate