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Difuncionalización aminativa enantioselectiva y catalítica de los alquenos

Nan Huang¹, Jie Luo¹, Lihao Liao¹

¹Institute of Organic Chemistry and MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry, IGCME, Sun Yat-Sen University, Guangzhou 510006, China.

Journal of the American Chemical Society

|March 1, 2024

Resumen

Este estudio introduce un nuevo método catalizado por cobre para la difuncionalización aminativa enantioselectiva de alquenos utilizando compuestos azoicos. El enfoque sintetiza eficientemente valiosos derivados cíclicos de hidrazina con alta selectividad.

Área de la Ciencia:

Química orgánica
Catálisis asimétrica
Metodología sintética

Sus antecedentes:

La difuncionalización enantioselectiva de los alquenos es crucial para la síntesis de moléculas enriquecidas con enantio.
La difuncionalización aminativa enantioselectiva, especialmente a través de la adición electrofílica, sigue siendo un desafío significativo en la síntesis orgánica.

Objetivo del estudio:

Desarrollar un método nuevo, eficiente y enantioselectivo para la difuncionalización aminativa de alceno.
Para utilizar compuestos azo externos como fuentes de nitrógeno en una reacción de adición electrofílica catalizada por cobre.

Principales métodos:

Reacción de adición electrofílica catalizada por el cobre.
Utilizan compuestos azoicos externos como fuentes de nitrógeno.
Se utilizó un ligando quiral de cianoxazolina recientemente desarrollado para el control de la enantioselectividad.

Principales resultados:

Se logró una difuncionalización aminativa enantioselectiva sin precedentes de alquenos.
Sintetizó una variedad de derivados cíclicos de hidrazina con altas quimio-, regio-, enantio- y diastereoselectividades.
Demostró el amplio alcance de los nucleófilos, incluidos los grupos ácido carboxílico, hidroxi, amida, sulfonamida y arilo.

Conclusiones:

El método desarrollado catalizado por cobre proporciona una poderosa nueva estrategia para la síntesis enantioselectiva.
El nuevo ligando de cianoxazolina es clave para lograr una alta enantioselectividad en esta transformación.
Este enfoque ofrece una vía versátil para obtener valiosos derivados cíclicos de hidrazina.

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