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Pyro-boratos, espiro-boratos y boroxinatos de BINOL: ensamblaje, estructuras y reactividad

Gang Hu¹, Anil K Gupta¹, Li Huang¹

¹Department of Chemistry, Michigan State University , East Lansing, Michigan 48824, United States.

Journal of the American Chemical Society

|June 29, 2017

Resumen

El estudio revela que los ligandos de BINOL forman varias especies de boratos, incluidos los boroxinatos y los espiroboratos, que pueden actuar como catalizadores asimétricos eficaces. Los derivados específicos de BINOL, como el 3,3′-Ph2BINOL, obtienen un rendimiento catalítico superior en las reacciones de aziridinación.

Área de la Ciencia:

Química organometálica
Catálisis asimétrica
Química del boro

Sus antecedentes:

Los ligandos VANOL y VAPOL forman catalizadores efectivos de boroxinato con B ((OPh) 3.
Anteriormente se descubrió que los ligandos de BINOL, a diferencia de VANOL/VAPOL, eran malos catalizadores con B ((OPh) 3).
Los ésteres de borato de BINOL son catalizadores quirales conocidos, que existen en varias formas como meso-boratos y espiro-boratos.

Objetivo del estudio:

Investigar las estructuras de los ésteres de borato derivados del BINOL formados con estequiometría variable de B ((OPh) 3.
Evaluar la actividad catalítica y la inducción asimétrica de estas especies de borato de BINOL.
Comprender cómo los diferentes derivados de BINOL y las condiciones de reacción influyen en la formación de especies catalíticas.

Principales métodos:

Síntesis de ésteres de borato de BINOL utilizando diferentes proporciones molares de BINOL y B ((OPh)) 3.
Caracterización estructural de las especies de borato resultantes (piroborato, espiroborato y boroxinato).
Evaluación del rendimiento catalítico en reacciones asimétricas de aziridinación.

Principales resultados:

BINOL puede formar especies de boroxinato y espiro-borato, a diferencia de lo que se suponía anteriormente.
Estas especies de borato de BINOL pueden exhibir actividad catalítica, a veces con inducciones asimétricas opuestas.
Los derivados 3,3'-disubstituidos de BINOL, en particular el 3,3'-Ph2BINOL, forman catalizadores efectivos de boroxinato para la aziridinación asimétrica.

Conclusiones:

Las especies de borato derivadas de BINOL no son inherentemente catalizadores inferiores; su estructura y rendimiento dependen de las condiciones de reacción y la sustitución del ligando.
La formación de estructuras específicas de borato (boroxinato, espiro-borato) dicta los resultados catalíticos.
Los ligandos BINOL sustituidos ofrecen propiedades catalíticas sintonizables, con grupos estéricamente exigentes en las posiciones 3,3 'que potencialmente obstaculizan la formación de catalizadores.

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