title: Selective amination reactions of α-nitro aryl and heteroaryl enoates.
abstract: Highly functionalized tetrasubstituted alkenes were obtained by an unexpected amination reaction promoted by ethyl nosyloxycarbamate on various α-nitro aryl and heteroaryl enoates. A nitrene is likely the aminating species responsible for the observed insertion reaction leading to (E)-β-amino α-nitro enoates as the major products, regardless of the substrate configuration. The compounds, bearing two nitrogenous functional groups in different oxidation states, can be regarded as interesting synthons. In contrast, aziridination was observed for α-nitro alkyl enoates or β-nitro allylic alcohols.
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Roma La Sapienza, P.le A. Moro 5, I-00185 Roma, Italy. stefania.fioravanti@uniroma1.it.
authors.forename: Stefania
authors.initials: S
authors.lastname: Fioravanti
authors.forename: Lucio
authors.initials: L
authors.lastname: Pellacani
authors.forename: Maria Cecilia
authors.initials: MC
authors.lastname: Vergari
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000586:Amination; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*
chemical_list: D000475:Alkenes; D004952:Esters; D009574:Nitro Compounds