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Acoplamiento reductivo intermolecular regioselectivo y enantioselectivo catalizado por níquel de alquenos alifáticos

Zhi-Hong Chen¹, Li-Jie Gu¹, Biao Wang¹

¹State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Nankai University, Tianjin 300071, China.

Journal of the American Chemical Society

|May 23, 2024

Resumen

Este estudio presenta un nuevo método catalizado por níquel para acoplar alquenos e iminas no activados. La reacción produce eficientemente aminas quirales con alta selectividad, utilizando nuevos ligandos de fosfina quirales.

Área de la Ciencia:

Química orgánica
Catálisis
Síntesis asimétrica

Sus antecedentes:

Los alquenos alifáticos no activados son materiales de partida valiosos debido a su disponibilidad.
El acoplamiento reductor enantioselectivo intermolecular de alquenos no activados con iminas sigue siendo un desafío sintético significativo.

Objetivo del estudio:

Desarrollar un método eficiente para el acoplamiento reductor intermolecular catalizado por níquel de alquenos e iminas no activados.
Para lograr elevadas enantioselectividades y selectividades lineales en la síntesis de aminas quirales.

Principales métodos:

Utilizando un sistema de catalizador de níquel.
Utilizando ligandos de espirofosfina quirales monodentados recientemente desarrollados.
Investigando el acoplamiento de una amplia gama de alquenos alifáticos con iminas.

Principales resultados:

Desarrollo exitoso de un método de acoplamiento reductivo intermolecular catalizado por níquel.
Se han obtenido excelentes enantioselectividades y buenas selectividades lineales para los productos de aminas quirales.
Compatibilidad demostrada con diversos alquenos alifáticos, incluidos los de moléculas bioactivas.

Conclusiones:

El método desarrollado proporciona una vía eficaz para obtener aminas quirales a partir de materiales de partida fácilmente disponibles.
El uso de nuevos ligandos quirales de espirofosfina es crucial para el éxito de la reacción.
Este enfoque expande la utilidad sintética de los alquenos no activados en la síntesis asimétrica.

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