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Fluoroaminación catalítica y enantioselectiva de los alquenos
Katrina M Mennie1, Steven M Banik1, Elaine C Reichert1
1Department of Chemistry & Chemical Biology , Harvard University , Cambridge , Massachusetts 02138 , United States.
Journal of the American Chemical Society
|March 28, 2018
Resumen
Este estudio informa de un nuevo método para sintetizar bloques de construcción quirales fluorados utilizando un catalizador. Este enfoque proporciona un acceso altamente selectivo a valiosos compuestos fluoroorgánicos para el descubrimiento de fármacos.
Área de la Ciencia:
- Química orgánica
- Síntesis asimétrica
- Química de la fluoración
Sus antecedentes:
- Los compuestos orgánicos fluorados quirales son componentes cruciales en la química medicinal.
- El desarrollo de métodos eficientes y estereoselectivos para su síntesis sigue siendo un desafío importante.
Objetivo del estudio:
- Desarrollar un nuevo sistema catalítico para la síntesis estereoselectiva de derivados de la sin-β-fluoroaziridina.
- Explorar la utilidad de este método para acceder a otros compuestos fluorados con múltiples estereocentros.
Principales métodos:
- Fluoración de aminas alilicas catalizada por el yoduro de arilo quiral utilizando HF-piridina y mCPBA.
- Utilización de la diastereoselectividad controlada por catalizadores para la síntesis de aminas fluoradas complejas.
- Aplicación del método desarrollado a diversos sustratos de alquenos.
Principales resultados:
- Alta diastereoselectividad y enantioselectividad en la síntesis de las β-fluoroaziridinas.
- Preparación exitosa de 1,3-difluoro-2-aminas enriquecidas con enantio con tres estereocentros contiguos.
- Acceso a las anti-β-fluorpirrolidinas y a los productos 1,2-oxifluorados procedentes de diversos sustratos.
Conclusiones:
- El catalizador de ioduro de arilo quiral desarrollado permite una síntesis estereoselectiva eficiente de bloques de construcción fluoroorgánicos valiosos.
- El método ofrece una amplia aplicabilidad para acceder a moléculas fluoradas complejas con múltiples estereocentros.
- Este trabajo proporciona una herramienta poderosa para la síntesis de productos farmacéuticos y agroquímicos fluorados.
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