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Título

A case study of thiourea-assisted iminium formation by hydroxyl anion binding: Kinetic, spectroscopic and computational evidences

AutorJuste-Navarro, Verónica CSIC ORCID; Prieto, Liher; Delso, J. Ignacio CSIC ORCID; Manzano, Rubén; Tejero, Tomás CSIC ORCID; Reyes, Efraim; Vicario, Jose L.; Merino, Pedro CSIC ORCID
Palabras claveThioureas
Iminium catalysis
Nitrones
Hydroxide binding
Squaramides
Fecha de publicación2017
EditorWiley-VCH
CitaciónAdvanced Synthesis and Catalysis 359(23): 4122-4128 (2017)
ResumenThe 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.
Versión del editorhttps://doi.org/10.1002/adsc.201700986
URIhttp://hdl.handle.net/10261/184748
DOI10.1002/adsc.201700986
ISSN1615-4150
E-ISSN1615-4169
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