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Síntesis asimétrica catalizada por ácido fosfórico de derivados de SPINOL

Shaoyu Li^1,2, Ji-Wei Zhang¹, Xian-Lin Li¹

¹Department of Chemistry, South University of Science and Technology of China , Shenzhen 518055, China.

Journal of the American Chemical Society

|December 10, 2016

Resumen

Los investigadores desarrollaron una nueva síntesis asimétrica catalizada por ácido fosfórico para derivados quirales de 1,1'-spirobiindano-7,7'-diol (SPINOL). Este método eficiente proporciona acceso a estructuras privilegiadas de SPINOL con alto rendimiento y enantioselectividad, incluso con baja carga de catalizador.

Área de la Ciencia:

Química orgánica
Síntesis asimétrica
Catálisis

Sus antecedentes:

El 1,1'-espirobiindano-7,7'-diol axialmente quiral (SPINOL) es una estructura privilegiada crucial.
Los derivados de SPINOL sirven como componentes esenciales para varios ligandos quirales.

Objetivo del estudio:

Desarrollar el primer enfoque asimétrico catalizado por ácido fosfórico para la síntesis de derivados de SPINOL.
Proporcionar un método práctico y eficiente para acceder a las estructuras de SPINOL enriquecidas enantioméricamente.

Principales métodos:

Desarrollo de una nueva reacción asimétrica catalizada por ácido fosfórico.
Demostración de una alta tolerancia y convergencia del grupo funcional.
Aplicación de un catalizador de ácido 4,4'-dimetilo-SPINOL-fosfórico sintetizado.

Principales resultados:

Síntesis eficiente de SPINOLs con alto rendimiento y excelente enantioselectividad.
Reducción exitosa de la carga del catalizador a 0,1 mol% para la síntesis a escala preparativa.
Demostración de la utilidad del catalizador en la síntesis de derivados de SPINOL enriquecidos con enantio.

Conclusiones:

El método desarrollado ofrece un acceso directo y práctico a la estructura privilegiada de SPINOL.
Este enfoque hace avanzar significativamente la síntesis enantioselectiva de los derivados de SPINOL.
La baja carga del catalizador destaca la eficiencia y escalabilidad del método.

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