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Fluoración asimétrica de las enamidas: acceso a las α-fluoroiminas mediante un catalizador de transferencia de fase

Robert J Phipps¹, Kenichi Hiramatsu, F Dean Toste

¹Department of Chemistry, University of California, Berkeley, 94720, United States.

Journal of the American Chemical Society

|May 12, 2012

Resumen

La catálisis quiral de transferencia de fase permite la fluoración enantioselectiva de las enamidas utilizando Selectfluor. Este método proporciona acceso a valiosas α-(fluoro) benzoiliminas, precursores de las β-fluoroaminas estereodefinidas cruciales en la síntesis farmacéutica.

Área de la Ciencia:

Química orgánica es la química orgánica.
Catalización asimétrica por catálisis asimétrica.
Fluoración Química de la fluoración

Sus antecedentes:

La síntesis enantioselectiva de compuestos orgánicos fluorados es crucial para el descubrimiento de fármacos.
Desarrollar métodos catalíticos eficientes para introducir átomos de flúor estereoselectivamente sigue siendo un desafío significativo.
La catálisis quiral de transferencia de fase ofrece una estrategia prometedora para las transformaciones asimétricas en medios no polares.

Objetivo del estudio:

Desarrollar un nuevo método de fluoración enantioselectiva para las enamidas.
Para utilizar un fosfato derivado de BINOL como catalizador de transferencia de fase aniónica quiral.
Para sintetizar las versátiles α-(fluoro) benzoiliminas con alta enantioselectividad.

Principales métodos:

Empleando un fosfato derivado de BINOL como catalizador de transferencia de fase aniónica quiral.
Utilizando Selectfluor como el reactivo fluorante electrófilo.
Realizar la reacción en un disolvente no polar para facilitar la catálisis de transferencia de fase.

Principales resultados:

Se logró una fluoración enantioselectiva exitosa de una amplia gama de enamidas.
Se obtuvieron altas enantioselectividades para la formación de α-(fluoro) benzoiliminas.
Los compuestos sintetizados son estables y sintéticamente versátiles.

Conclusiones:

El método desarrollado proporciona un acceso eficiente a las α-(fluoro) benzoiliminas enriquecidas enantioméricamente.
Estos productos sirven como valiosos precursores para las β-fluoroaminas altamente estereodefinidas.
La metodología tiene un potencial significativo para aplicaciones de síntesis farmacéutica.

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