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Cicloadición asimétrica de azido-alquino con catálisis cooperativa de ir {I) / cuadramida: síntesis atroposelectiva

Xue Zhang¹, Shunian Li¹, Wenjing Yu¹

¹Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan 250100, China.

Journal of the American Chemical Society

|April 4, 2022

Resumen

Un nuevo sistema catalítico cooperativo que utiliza Iridium ((I) y squaramide permite la primera síntesis atroposelectiva de ariltriazoles axialmente quirales. Este método proporciona acceso a estructuras únicas de ariltriazol con alto rendimiento y enantioselectividad.

Área de la Ciencia:

Química orgánica
Catálisis
Síntesis asimétrica

Sus antecedentes:

Los ariltriazoles axialmente quirales son motivos estructurales importantes.
Los métodos tradicionales como las reacciones de clic tienen limitaciones en el acceso a diversos esqueletos de ariltriazol.
El desarrollo de nuevas estrategias catalíticas es crucial para una síntesis eficiente.

Objetivo del estudio:

Desarrollar una nueva estrategia catalítica cooperativa para la síntesis atroposelectiva de ariltriazoles axialmente quirales.
Explorar el uso de un sistema de iridio (I) / cuadramida para esta transformación.
Para sintetizar esqueletos de ariltriazol diversos y estructuralmente nuevos.

Principales métodos:

Utilizó un sistema catalítico cooperativo de iridio y cuadramida.
Se utilizan cuadramidas naturales derivadas de la quinidina y la quinina como auxiliares quirales.
Se investigó el mecanismo de reacción, incluida la activación de la coordinación y el potencial de autoextinción.

Principales resultados:

Logró la primera síntesis atroposelectiva de ariltriazoles axialmente quirales.
Se han sintetizado diversos esqueletos de ariltriazol con buenos rendimientos y una excelente enantioselectividad.
Se demostró que ambos enantiómeros se pueden obtener fácilmente.
Se ha observado una activación significativa de la coordinación Ir{\displaystyle I}/squaramida sin autoapagamiento.

Conclusiones:

El desarrollo de la catálisis cooperativa Ir{I}/squaramida es una poderosa estrategia para la síntesis atroposelectiva de ariltriazol.
Este método supera las limitaciones de las reacciones de clic tradicionales, permitiendo el acceso a estructuras únicas.
El sistema muestra una activación cooperativa eficiente y es versátil para obtener ambos enantiómeros.

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