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Hidrogenación altamente enantioselectiva de alquenos catalizada por el hierro

Peng Lu¹, Xiang Ren¹, Haofeng Xu¹

¹Department of Chemistry, Zhejiang University, 310058 Hangzhou, China.

Journal of the American Chemical Society

|August 3, 2021

Resumen

Este estudio introduce un nuevo método catalizado por hierro para la hidrogenación enantioselectiva de alquenos, produciendo alcanos quirales con alta selectividad y eficiencia. El protocolo desarrollado es simple, utiliza baja presión de hidrógeno y demuestra una amplia tolerancia de grupo funcional.

Área de la Ciencia:

Química orgánica
Catálisis
Síntesis asimétrica

Sus antecedentes:

Los alcanos quirales son bloques de construcción valiosos en productos farmacéuticos y materiales.
El desarrollo de métodos catalíticos eficientes para su síntesis sigue siendo un desafío importante.
La catálisis del hierro ofrece una alternativa sostenible y rentable a los catalizadores de metales preciosos.

Objetivo del estudio:

Para informar de la primera hidrogenación altamente enantioselectiva catalizada por hierro de alquenos 1,1-disubstituidos.
Desarrollar un nuevo ligando quiral y su complejo de hierro para esta transformación.
Investigar el mecanismo y el alcance de la reacción.

Principales métodos:

Diseño y síntesis de un nuevo ligando quiral de 8-oxazolina e iminoquinolina.
Preparación del complejo de hierro del ligando.
Hidrogenación enantioselectiva de alquenos 1,1-disubstituidos mínimamente funcionalizados utilizando 1 atm de H2.
Experimentos de etiquetado de deuterio para sondear el mecanismo.

Principales resultados:

Se ha logrado una conversión completa y una excelente enantioselectividad (ee) para la hidrogenación de alquenos 1,1-disubstituidos.
Se ha demostrado una buena tolerancia del grupo funcional del sistema catalítico.
Propuso un mecanismo primario para la hidrogenación enantioselectiva catalizada por hierro.

Conclusiones:

El catalizador de hierro desarrollado permite una síntesis eficiente y altamente enantioselectiva de alcanos quirales a partir de alquenos simples.
El protocolo es operacionalmente simple y respetuoso con el medio ambiente.
Este trabajo proporciona una nueva vía para la hidrogenación asimétrica catalizada por hierro.

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