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Funcionalización del enantioselectivo Domino Heck catalizado por paladio / enlace C-H intermolecular: desarrollo y

Wangqing Kong¹, Qian Wang¹, Jieping Zhu¹

¹Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne , EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland.

Journal of the American Chemical Society

|December 19, 2015

Resumen

Este estudio introduce un nuevo método para sintetizar oxindoles 3,3-disubstituidos de alta enantioselectividad. La estrategia desarrollada de carbopaladación asimétrica y captura de azoles crea eficientemente estereocentros cuaternarios, lo que demuestra una amplia aplicabilidad en la síntesis orgánica.

Área de la Ciencia:

Química orgánica
Síntesis asimétrica
Catálisis

Sus antecedentes:

Los oxíndolos son bastidores heterocíclicos cruciales en la química medicinal.
La construcción eficiente de estereocentros cuaternarios de todo carbono sigue siendo un desafío sintético.

Objetivo del estudio:

Desarrollar una nueva síntesis asimétrica para oxindoles 3,3-disubstituidos.
Establecer un método para crear estereocentros cuaternarios a través de la formación de enlaces C-C.
Para explorar la transformación posterior de los oxindoles en pirroloindolinas.

Principales métodos:

Carbopaladación asimétrica intramolecular de las N-ariloacrilamidas.
Captura intermolecular de complejos de paladio con azoles.
Ciclización reductora para la síntesis de pirroloindolina.

Principales resultados:

Se obtienen buenos rendimientos y excelentes enantioselectividades para los oxindoles 3,3-disubstituidos.
Se crearon con éxito dos enlaces C-C y un estereocentro cuaternario de carbono.
Demostró la conversión a pirroloindolinas y aplicó la metodología para sintetizar (+) -sermetolo.

Conclusiones:

La metodología desarrollada proporciona una vía eficiente para obtener oxindoles 3,3-disubstituidos enantioméricamente enriquecidos.
La estrategia permite la construcción de arquitecturas moleculares complejas.
Destaca el potencial de la catálisis del paladio en la síntesis asimétrica.

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