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Una propargilación asimétrica general catalizada por cobre-BINAP de cetonas con boronatos de propargilo catalizados
Keith R Fandrick1, Daniel R Fandrick, Jonathan T Reeves
1Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. keith.fandrick@boehringer-ingelheim.com
Journal of the American Chemical Society
|June 7, 2011
Resumen
Un nuevo catalizador de cobre-BINAP permite la propargillación altamente enantioselectiva de las cetonas. Este método versátil produce aductos de homopropargil, precursores útiles para la síntesis de varios compuestos orgánicos valiosos.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- La catálisis de la catálisis.
- Síntesis asimétrica de síntesis.
Sus antecedentes:
- La síntesis enantioselectiva es crucial para los productos farmacéuticos y los productos químicos finos.
- El desarrollo de sistemas catalíticos eficientes para la formación de enlaces carbono-carbono sigue siendo un desafío clave.
Objetivo del estudio:
- Desarrollar un método operacionalmente simple y altamente enantioselectivo para la propargilación de cetonas.
- Para explorar el alcance del sustrato y la utilidad sintética de los aductos de homopropargyl resultantes.
Principales métodos:
- El cobre-BINAP catalizó la propargillación enantioselectiva de las cetonas procirales.
- Utilizado metil etil cetona como un modelo de sustrato.
- Investigó la transformación de los aductos obtenidos en otros grupos funcionales.
Principales resultados:
- Se ha logrado una alta enantioselectividad en la propargilación de varias cetonas procirales.
- Demostró la aplicabilidad del método a una amplia gama de sustratos.
- Convierte con éxito los aductos de homopropargilo en γ-butirolactonas, β-hidroxi-metilcetonas y β-hidroxicarboxilatos.
Conclusiones:
- La reacción catalizada por cobre-BINAP desarrollada ofrece una ruta directa y altamente enantioselectiva a los aductos de homopropargyl.
- Estos aductos sirven como versátiles intermedios para la síntesis de valiosas moléculas orgánicas.
- Esta metodología amplía el conjunto de herramientas para la síntesis asimétrica de estructuras orgánicas complejas.
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