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Catálisis de cobalto para la construcción de ciclobutanona enantioselectiva

Daniel K Kim¹, Jan Riedel¹, Raphael S Kim¹

¹Department of Chemistry, University of California, Irvine , Irvine, California 92697, United States.

Journal of the American Chemical Society

|July 14, 2017

Resumen

Este estudio introduce un catalizador de cobalto para la síntesis de ciclobutanonas mediante hidroacilación intramolecular. El catalizador ofrece un excelente control de la reacción en condiciones suaves, superando las limitaciones anteriores.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Las reacciones de hidroacilación intramoleculares tradicionalmente favorecen la formación de anillos de cinco miembros sobre los anillos de cuatro miembros.
El desarrollo de métodos eficientes para la síntesis de ciclobutanonas sigue siendo un desafío importante en la química orgánica.

Objetivo del estudio:

Desarrollar un nuevo sistema catalítico para la síntesis eficiente de ciclobutanonas.
Para lograr una alta regioselectividad, diastereoselectividad y enantioselectividad en la formación de ciclobutanona.
Para utilizar metales abundantes en la tierra para transformaciones sintéticas sostenibles.

Principales métodos:

Utilizando un catalizador derivado del cobalto abundante en la tierra para la hidroacilación intramolecular.
Optimización de las condiciones de reacción, incluida la carga del catalizador (2 mol %) y la temperatura (hasta 50 °C).
Caracterización de los productos de ciclobutanona sintetizados para confirmar la estructura y la estereoquímica.

Principales resultados:

Síntesis exitosa de ciclobutanonas utilizando el catalizador de cobalto.
Demostración de un excelente control regioquímico, favoreciendo la formación de anillos de cuatro miembros.
Se obtuvieron altos niveles de diastereoselectividad y enantioselectividad en los productos de ciclobutanona.
La reacción procede eficientemente en condiciones suaves, mostrando la robustez del catalizador.

Conclusiones:

Un nuevo catalizador basado en cobalto permite la síntesis eficiente de ciclobutanonas a través de la hidroacilación intramolecular.
Este método supera la preferencia histórica por la formación de anillos de cinco miembros, proporcionando acceso a valiosos carbociclos de cuatro miembros.
El rendimiento del catalizador en condiciones suaves y su derivación del cobalto abundante en la tierra resaltan su potencial para la síntesis orgánica sostenible.

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