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Ciclizaciones en cascada biomiméticas iniciadas por acilnitrenoides de iridio: acceso estereodeterminado a los

Eleonora Tufano¹, Euijae Lee^2,3, Matteo Barilli¹

¹Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy.

Journal of the American Chemical Society

|November 6, 2023

Resumen

Los investigadores desarrollaron una nueva ciclización en cascada biomimética para sintetizar azaciclos fusionados en anillos. Este método eficiente utiliza arylalkenyl dioxazolones, que ofrece un amplio alcance de sustrato y una alta estereoselectividad para crear moléculas complejas.

Área de la Ciencia:

Química orgánica
Química sintética
Química medicinal

Sus antecedentes:

Los compuestos azacíclicos fusionados en anillo son andamios cruciales en productos farmacéuticos y naturales.
Los métodos sintéticos existentes a menudo carecen de eficiencia o amplia aplicabilidad.

Objetivo del estudio:

Desarrollar una nueva ciclización en cascada biomimética para sintetizar diversos azaciclos fusionados en anillos.
Explorar el alcance y las limitaciones de esta nueva estrategia sintética.

Principales métodos:

Ciclificación en cascada biomimética de las arylalkenil dioxazolonas.
Transferencia intramolecular de un iridio-acilnitrenoide a un enlace doble olefínico.
Formación y posterior reacción de un intermediario de N-acilaziridina.

Principales resultados:

Se obtiene una excelente estereoselectividad y una alta tolerancia de grupo funcional.
Se ha demostrado un alcance de sustrato flexible, que incluye fracciones heteroariles y alquiniles.
Sintetizó con éxito varios compuestos azacíclicos fusionados en anillos con alta regioselectividad y estereoselectividad.

Conclusiones:

La ciclización en cascada biomimética desarrollada proporciona una ruta eficiente y versátil para azaciclos complejos.
Este método ofrece una herramienta poderosa para la síntesis de moléculas y materiales biológicamente relevantes.
El mecanismo de reacción involucra un intermediario clave de N-acilaziridina, destacando una nueva vía sintética.

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