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J Org Chem. 2011 Apr 1;76(7):2240-4. doi: 10.1021/jo101599q. Epub 2011 Mar 7.

Dihydropyranone formation by ipso C-H activation in a glucal 3-carbamate-derived rhodium acyl nitrenoid.

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  • 1Department of Chemistry, Barnard College, 3009 Broadway, New York, New York 10027, USA.


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.

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