A case study of Thiourea-assisted Iminium formation by hydroxyl anion binding: kinetic, spectroscopic and computational evidences
Resumen: The experimental and computational study of the mechanism of the iminium-organocatalyzed formation of N-hydroxypyrrolidines from nitrones, revealed up to three activation levels of the Schreiner''s thiourea used as co-catalyst, i.e: (i) formation of the iminium ion through hydroxyl anion recognition forming a stable ion pair; (ii) enolization of the nitrone through a H-bond network and (iii) activation of the nitrone moiety towards the final ring closure. The computational model supports the mechanism and the catalytic cycle. This mechanistic rationale is supported by the lack of reactivity of preformed iminium ion with the nitrone in the absence of thiourea-hydroxyl complex and the observed reactivity when a complex thiourea-tetrabutylammonium hydroxide is added. (Figure presented.).
Idioma: Inglés
DOI: 10.1002/adsc.201700986
Año: 2017
Publicado en: Advanced Synthesis and Catalysis 359, 23 (2017), 4122-4128
ISSN: 1615-4150

Factor impacto JCR: 5.123 (2017)
Categ. JCR: CHEMISTRY, ORGANIC rank: 7 / 57 = 0.123 (2017) - Q1 - T1
Categ. JCR: CHEMISTRY, APPLIED rank: 3 / 71 = 0.042 (2017) - Q1 - T1

Factor impacto SCIMAGO: 2.079 - Organic Chemistry (Q1) - Catalysis (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E10
Financiación: info:eu-repo/grantAgreement/ES/MINECO/CTQ2014-52107-P
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2016-76155-R
Tipo y forma: Article (PostPrint)
Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)
Exportado de SIDERAL (2019-07-09-12:42:08)


Visitas y descargas

Este artículo se encuentra en las siguientes colecciones:
articulos



 Notice créée le 2018-12-12, modifiée le 2019-07-09


Postprint:
 PDF
Évaluer ce document:

Rate this document:
1
2
3
 
(Pas encore évalué)