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Síntesis asimétrica de nitrógeno a través de la hidroaminación de tipo Cope catalizada por ligando del ciclopropeno

Zhanyu Li¹, Jinbo Zhao¹, Baozhen Sun¹

¹Jilin Province Key Laboratory of Functional Organic Molecule Design & Synthesis, Department of Chemistry, Northeast Normal University , Changchun, Jilin 130024, China.

Journal of the American Chemical Society

|August 8, 2017

Resumen

Los investigadores desarrollaron un nuevo método catalítico para la síntesis asimétrica de nitrón utilizando la hidroaminación de oxima. Este proceso enantioselectivo ofrece un alto control y un amplio alcance para crear nitrones quirales.

Área de la Ciencia:

Química orgánica
Catálisis
Síntesis asimétrica

Sus antecedentes:

Los nitrones quirales son valiosos intermedios sintéticos.
Los métodos existentes para la síntesis de nitrón a menudo carecen de enantioselectividad o amplia aplicabilidad.

Objetivo del estudio:

Desarrollar la primera hidroaminación enantioselectiva de oximas tipo Cope para la síntesis asimétrica de nitrón.
Establecer un nuevo sistema catalítico para la formación eficiente y controlada de nitrón quiral.

Principales métodos:

Utilizó un sistema catalítico basado en cobre con un ligando específico.
Se utilizan materiales de partida fácilmente disponibles y condiciones de reacción suaves.
Investigó el mecanismo de reacción a través de estudios preliminares.

Principales resultados:

Logró la primera hidroaminación enantioselectiva tipo Cope de oximas.
Se ha demostrado un amplio alcance y un alto control enantio y diastereo en la síntesis asimétrica de nitrón.
Se identificó una aminocupración olefin metalla-retro-Cope como el paso clave para la formación de enlaces C-N.

Conclusiones:

Este trabajo presenta un método conceptualmente novedoso y altamente eficaz para la formación catalítica de nitrones.
La metodología desarrollada avanza significativamente en la síntesis quiral de nitrón, ofreciendo una ruta más eficiente.
Se espera que los hallazgos estimulen una mayor investigación en catálisis asimétrica y química del nitrón.

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