title: Metal-free oxyaminations of alkenes using hydroxamic acids.
abstract: A radical-mediated approach to metal-free alkene oxyamination is described. This method capitalizes on the unique reactivity of the amidoxyl radical in alkene additions to furnish a general difunctionalization using simple diisopropyl azodicarboxylate (DIAD) as a radical trap. This protocol capitalizes on the intramolecular nature of the process, providing single regioisomers in all cases. Difunctionalizations of cyclic alkenes provide trans oxyamination products inaccessible using current methods with high levels of stereoselectivity, complementing cis-selective oxyamination processes.
authors: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA.
authors: Valerie A
authors: VA
authors: Schmidt
authors: Erik J
authors: EJ
authors: Alexanian
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006877:Hydroxamic Acids / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001391:Azo Compounds; D006877:Hydroxamic Acids