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Cícloadición azida-alquina catalizada por el cobre asimétrico (I) a los oxindoles cuaternarios

Feng Zhou¹, Chen Tan, Jing Tang

¹Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China.

Journal of the American Chemical Society

|July 17, 2013

Resumen

Los investigadores desarrollaron una reacción catalizada por el cobre para crear moléculas complejas. Este método produce de manera eficiente oxindoles cuaternarios quirales con alta enantioselectividad, un paso clave en la síntesis de compuestos valiosos.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Síntesis asimétrica de síntesis.

Sus antecedentes:

Los oxindoles cuaternarios son importantes motivos estructurales en los productos farmacéuticos.
Desarrollar métodos eficientes para su síntesis asimétrica sigue siendo un desafío.

Objetivo del estudio:

Informar sobre una nueva cicloadición azida-alquina catalizada por el cobre enantioselectivo (I).
Para lograr una desimetrización asimétrica de las 1,6-heptadiinas basadas en oxindoles.

Principales métodos:

Se utilizó un catalizador de cobre para la cicloadición azida-alquina.
Empleó 1,6-heptadiinas basadas en oxindoles como sustratos.
Se logró una desimetrización asimétrica para formar centros cuaternarios.

Principales resultados:

Se han sintetizado con éxito oxindoles cuaternarios que contienen una fracción de 1,2,3-triazol.
Se logra una alta enantioselectividad, con un exceso enantiomérico (ee) que oscila entre el 84% y el 98%.

Conclusiones:

El método desarrollado proporciona una ruta eficiente a los oxindoles cuaternarios enriquecidos enantioméricamente.
Este enfoque ofrece una herramienta valiosa para acceder a moléculas quirales complejas.

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