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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
Published on: January 17, 2020
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Plegamiento enantioselectivo de Enynes por oro (I) Catalizadores con un elemento quiral remoto
Giuseppe Zuccarello1,2, Joan G Mayans1,2, Imma Escofet1,2
1Institute of Chemical Research of Catalonia (ICIQ) , Barcelona Institute of Science and Technology , Av. Països Catalans 16 , 43007 Tarragona , Spain.
Journal of the American Chemical Society
|July 11, 2019
Resumen
Los nuevos catalizadores de oro quiral permiten la ciclización enantioselectiva de las 1,6-eninas. Estos catalizadores se utilizaron en la primera síntesis total de productos naturales de carexano, demostrando el control de la estereoquímica a través del plegamiento del sustrato.
Área de la Ciencia:
- Química organometálica
- Catálisis asimétrica
- Síntesis de productos naturales
Sus antecedentes:
- Los catalizadores de oro quiral son cruciales para la síntesis asimétrica.
- El diseño de ligandos quirales efectivos es clave para controlar la enantioselectividad.
- Las 1,6-eninas son sustratos versátiles para las reacciones de ciclización.
Objetivo del estudio:
- Diseñar nuevos catalizadores de oro quiral con una cavidad de unión a medida.
- Aplicar estos catalizadores para la ciclización enantioselectiva de las 1,6-eninas.
- Para lograr la primera síntesis total enantioselectiva de los productos naturales de carexano.
Principales métodos:
- Síntesis de un ligando JohnPhos modificado con una C2-2,5-diarilpirrolidina distal.
- Desarrollo de catalizadores quirales mononucleares de oro.
- Aplicación de catalizadores en las ciclizaciones 5-exo-dig y 6-endo-dig de 1,6-eninas.
- Análisis estereoquímico y síntesis total de productos naturales.
Principales resultados:
- Los catalizadores diseñados promueven efectivamente las ciclizaciones enantioselectivas 5-exo-dig y 6-endo-dig.
- Síntesis total enantioselectiva exitosa de tres miembros de la familia de los carexanos.
- Demostración de enantioselectividades opuestas en reacciones análogas debido al plegamiento del sustrato y a las interacciones arilo-arilo.
Conclusiones:
- Los nuevos catalizadores de oro quiral con un elemento quiral C2 proporcionan una alta enantioselectividad en ciclizaciones de 1,6-enino.
- El diseño del catalizador permite un control preciso de los resultados estereoquímicos.
- Este trabajo avanza en la catálisis asimétrica y en la síntesis de productos naturales.
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