On the dual reactivity of a Janus-type mesoionic dipole: experiments and theoretical validation

On the dual reactivity of a Janus-type mesoionic dipole: experiments and theoretical validation

A mesoionic bicycle, easily synthesized from a proteinogenic amino acid, l-leucine, behaves as both thiazolium-olate and diazolium-olate dipoles, as unveiled by its dipolar cycloadditions. This chameleonic reactivity has been thoroughly interpreted by dissecting the mechanistic landscape aided by th...

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Veröffentlicht in:Organic & biomolecular chemistry 2018, Vol.16 (26), p.4778-4783
Hauptverfasser: de la Concepción, Juan García, Ávalos, Martín, Cintas, Pedro, Jiménez, José L, Light, Mark E
Format: Artikel
Sprache:eng
Schlagworte:
Amino acids
Bicycles
Dipoles
Interaction models
L-leucine
Leucine
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Zusammenfassung:A mesoionic bicycle, easily synthesized from a proteinogenic amino acid, l-leucine, behaves as both thiazolium-olate and diazolium-olate dipoles, as unveiled by its dipolar cycloadditions. This chameleonic reactivity has been thoroughly interpreted by dissecting the mechanistic landscape aided by the distortion-interaction model.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob01195h