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Hidroboración enantioselectiva catalizada por cobre de alquenos 1,1-disubstituidos no activados
Won Jun Jang1, Seung Min Song1, Jong Hun Moon1
1Department of Chemistry and Institute of Basic Science, Sungkyunkwan University , Suwon 16419, Korea.
Journal of the American Chemical Society
|September 14, 2017
Resumen
Este estudio introduce un método catalítico eficiente para la hidroboración enantioselectiva de alquenos. El proceso produce productos enriquecidos enantioméricamente con alta selectividad y tolerancia al grupo funcional.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Síntesis asimétrica
Sus antecedentes:
- La hidroboración es una reacción clave en la síntesis orgánica.
- El desarrollo de métodos enantioselectivos para desafiar sustratos como los alquenos 1,1-disubstituidos sigue siendo un objetivo importante.
Objetivo del estudio:
- Desarrollar una hidroboración eficiente y altamente enantioselectiva de alquenos alifáticos 1,1-disubstituidos.
- Para lograr una fácil preparación de alquil pinacolboronatos β-quirales enriquecidos enantioméricamente.
Principales métodos:
- Se utilizó un catalizador fosfina-cobre para la reacción de hidroboración.
- Utilizó pinacolborano como fuente de boro.
- Investigó una variedad de alquenos 1,1-disubstituidos.
Principales resultados:
- Se obtiene una enantioselectividad elevada de hasta el 99% en la hidroboración.
- Se observó una enantiodiscriminación sin precedentes entre los sustituyentes alquilo geminales.
- Compatibilidad y eficiencia demostradas del grupo funcional a 1 mol % de carga del catalizador.
- Se realizó con éxito la síntesis a escala de gramos.
Conclusiones:
- La hidroboración catalizada por fosfina-Cu desarrollada es un método eficiente para sintetizar los alquil pinacolboronatos β-quirales enriquecidos enantioméricamente.
- El método muestra una excelente selectividad y una amplia aplicabilidad para diversos alquenos 1,1-disubstituidos.
- La baja carga del catalizador y la viabilidad a escala de gramos resaltan la utilidad práctica de esta transformación.
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