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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
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Ingreso enantioselectivo versátil catalizado por cobalto a los centros estereogénicos cuaternarios de todo el carbono
1Department of Chemistry , National University of Singapore , 3 Science Drive 3 , Singapore 117543 , Singapore.
Journal of the American Chemical Society
|August 17, 2018
Resumen
Los investigadores desarrollaron un nuevo método para crear γ-lactamas quirales borilo-funcionalizados con estereocentros cuaternarios de todo carbono utilizando catálisis de cobalto. Este avance permite la síntesis de diversos lactamos quirales y compuestos relacionados.
Área de la Ciencia:
- Química orgánica
- Síntesis asimétrica
- Catálisis
Sus antecedentes:
- Los γ-lactamas quirales son componentes importantes en la química medicinal.
- Los métodos eficientes para construir estereocentros cuaternarios de carbono son muy buscados.
- La síntesis asimétrica de moléculas orgánicas complejas sigue siendo un desafío significativo.
Objetivo del estudio:
- Desarrollar una nueva síntesis asimétrica para los γ-lactamas quirales funcionalizados por borilo.
- Establecer un método para crear estereocentros cuaternarios de carbono.
- Explorar la utilidad sintética de los productos obtenidos.
Principales métodos:
- Reacción de hidroboración y ciclización enantioselectiva catalizada por cobalto.
- Se utilizan como sustratos las 1,6-eninas atadas a las amidas.
- Las transformaciones posteriores de los productos quirales γ-lactámicos.
Principales resultados:
- Sintetizó con éxito γ-lactamas quirales borilo-funcionalizados con estereocentros cuaternarios de todo carbono.
- Se obtiene una alta enantioselectividad en el proceso de hidroboración/ciclización.
- Se ha demostrado la fácil conversión de los productos en diversos lactamos quirales, pirrolidina-2,3-diones y derivados de ácidos β-amino.
Conclusiones:
- La reacción co-catalizada desarrollada proporciona una ruta efectiva a los γ-lactamas enriquecidos con enantio.
- Este método ofrece acceso a valiosos productos intermedios quirales para otras aplicaciones sintéticas.
- El estudio amplía la caja de herramientas para la síntesis asimétrica de heterociclos complejos que contienen nitrógeno.
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