Stereoselective synthesis of C-ketosides by sequential intramolecular hydrogen atom transfer–intermolecular allylation reaction

✍ Scribed by Angeles Martín; Inés Pérez-Martín; Luis M. Quintanal; Ernesto Suárez

• Book ID: 104095543
• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 175 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.06.070

✦ Synopsis

A tandem 1,5 or 1,6 hydrogen atom transfer (HAT)-radical allylation using carbohydrate models is described. The HAT reaction generated a C-glycos-1-yl radical intermediate, which added to allyltri-nbutyltin with high diastereoselectivity, to give C-ketosides with the quaternary carbon carrying two differently functionalized tethers.