Dihydropyranone Formation by Ipso C−H Activation in a Glucal 3-Carbamate-Derived Rhodium Acyl Nitrenoid
| Autor: | Sarah E. Bernard, Shenjuti Chowdhury, Nadia C. Abascal, Elsy Santizo-Deleon, Christian M. Rojas, Abigail L. Smenton, Ritu Gupta, Lindsay M. Repka, Victoria Baranov, Brisa Hurlocker |
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| Rok vydání: | 2011 |
| Předmět: |
Ketone
Glycal Nitrene Carbonates chemistry.chemical_element Carbon–hydrogen bond activation Medicinal chemistry Article Catalysis Rhodium Tosyl Compounds chemistry.chemical_compound Organometallic Compounds Organic chemistry Glucal chemistry.chemical_classification Molecular Structure Organic Chemistry Hypervalent molecule Hydrogen Bonding Oxidants Calcium Gluconate Kinetics chemistry Potassium Carbamates |
| Zdroj: | The Journal of Organic Chemistry. 76:2240-2244 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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