Recent advances in the preparation of enantiomerically pure hydroxylamines from nitrones

Matute, R. (Universidad de Zaragoza) ; García-Viñuales, S. ; Hayes, H. ; Ghirardello, M. (Universidad de Zaragoza) ; Darù, A. ; Tejero, T. (Universidad de Zaragoza) ; Delso, I. (Universidad de Zaragoza) ; Merino, P. (Universidad de Zaragoza)

Resumen: This review covers the recent advances in the synthesis of enantiomerically pure hydroxylamine’s employing nitrones as starting materials. Nucleophilic additions of organometallic reagents to nitrones are the most common way for introducing a hydroxyamino group into carbon skeletons with the concomitant formation of a new carbon-carbon bond. Addition of nucleophiles derived from enolates, cyanide or fluorinated derivatives allows the preparation of complex structures. Radical additions and, in particular samarium diiodidemediated reductive coupling of nitrones with carbonyl compounds and a, ß-unsaturated esters have also been considered. All these approaches provide efficient methods of preparation of enantiomerically pure hydroxylamine’s that are valuable synthetic intermediates.

Idioma: Inglés

DOI: 10.2174/1570179412666150914200035

Año: 2016

Publicado en: CURRENT ORGANIC SYNTHESIS 13, 5 (2016), 669-686
ISSN: 1570-1794

Factor impacto JCR: 1.917 (2016)

Categ. JCR: CHEMISTRY, ORGANIC rank: 35 / 59 = 0.593 (2016) - Q3 - T2

Factor impacto SCIMAGO: 0.565 - Organic Chemistry (Q3) - Biochemistry (Q3)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E10
Financiación: info:eu-repo/grantAgreement/ES/MICINN/CTQ2013-44367-C2-1-P

Tipo y forma: Article (PostPrint)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)
Área (Departamento): Área Tecnologi. Medio Ambiente (Dpto. Ing.Quím.Tecnol.Med.Amb.)