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Hidrofuncionalización asimétrica diversa de alquenos internos alifáticos a través de la hidroboración regioselectiva
1Division of Chemical Sciences, Lawrence Berkeley National Laboratory, and Department of Chemistry, University of California , Berkeley, California 94720, United States.
Journal of the American Chemical Society
|May 12, 2016
Resumen
Este estudio introduce un método de dos pasos para crear diversos compuestos a partir de alquenos internos. El proceso logra una alta selectividad, lo que permite una síntesis eficiente de bloques de construcción químicos valiosos.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Metodología sintética
Sus antecedentes:
- Los alquenos internos alifáticos son materiales de partida muy versátiles.
- El logro de una alta regioselectividad y enantioselectividad en la funcionalización de alceno sigue siendo un desafío.
Objetivo del estudio:
- Desarrollar una nueva estrategia de dos pasos para la hidrofuncionalización de alquenos internos alifáticos.
- Lograr una elevada regioselectividad y enantioselectividad en los productos sintetizados.
- Ampliar el alcance de los compuestos accesibles a través de la derivación estereospecífica.
Principales métodos:
- Hidroboración asimétrica catalizada por el cobre de alquenos internos.
- Derivación estereospecífica de los boronatos secundarios a varios grupos funcionales.
- Utilizando estudios computacionales para comprender los orígenes de la selectividad.
Principales resultados:
- Síntesis exitosa de diversos compuestos que incluyen amidas, haluros de alquilo, alcoholes, aldehídos, arenos y heteroarenos.
- Se ha demostrado una elevada regioselectividad y enantioselectividad en el proceso de hidrofuncionalización.
- Estableció una plataforma versátil para acceder a moléculas enriquecidas enantioméricamente de alquenos internos.
Conclusiones:
- La estrategia presentada en dos etapas ofrece una vía eficiente para la hidrofuncionalización asimétrica de alquenos internos.
- El método proporciona acceso a una amplia gama de entidades químicas valiosas con un excelente control estéreo.
- Las ideas computacionales aclaran la base mecanicista de las selectividades observadas, guiando el diseño futuro del catalizador.
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