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.
By using (N-tosyloxy)-3-O-carbamoyl-D-glucal 10, which removes the need for a hypervalent n class="Chemical">iodine(III) oxidant, we provide evidence for rhodiumnitrenoid-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-complexedacyl nitrene.
Authors: Kenneth M. Engstrom; Mario R. Mendoza; Mauricio Navarro-Villalobos; David Y. Gin Journal: Angew Chem Int Ed Engl Date: 2001-03-16 Impact factor: 15.336
Authors: Timothy J Donohoe; Majid J Chughtai; David J Klauber; David Griffin; Andrew D Campbell Journal: J Am Chem Soc Date: 2006-03-01 Impact factor: 15.419