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. © 2013 American Chemical Society.

Selective amination reactions of α-nitro aryl and heteroaryl enoates / Fioravanti, Stefania; Pellacani, Lucio; Vergari, MARIA CECILIA. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 78:16(2013), pp. 8203-8207. [10.1021/jo4012859]

Selective amination reactions of α-nitro aryl and heteroaryl enoates

FIORAVANTI, Stefania;PELLACANI, Lucio;VERGARI, MARIA CECILIA
2013

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. © 2013 American Chemical Society.
2013
amination; enoates; nitrene
01 Pubblicazione su rivista::01a Articolo in rivista
Selective amination reactions of α-nitro aryl and heteroaryl enoates / Fioravanti, Stefania; Pellacani, Lucio; Vergari, MARIA CECILIA. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 78:16(2013), pp. 8203-8207. [10.1021/jo4012859]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/524799
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