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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

Adición catalítica enantioselectiva del tipo Minisci a los heteroarenos

Rupert S J Proctor¹, Holly J Davis¹, Robert J Phipps²

¹Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, UK.

Science (New York, N.Y.)

|April 7, 2018

Resumen

Este estudio introduce un nuevo método para crear moléculas quirales utilizando adiciones radicales a los heteroarenos básicos. El proceso logra una alta enantioselectividad y regioselectividad, simplificando la síntesis de componentes farmacéuticos complejos.

Área de la Ciencia:

Química orgánica
Química medicinal
Catálisis asimétrica

Sus antecedentes:

Los heteroarenos básicos son andamios cruciales en productos farmacéuticos y compuestos bioactivos.
Las adiciones de radicales de tipo minisci son clave para la elaboración de estos heteroarenos.
El control de la estereoquímica absoluta en las reacciones de Minisci sigue siendo un desafío sintético significativo.

Objetivo del estudio:

Desarrollar un nuevo método para las adiciones asimétricas de tipo Minisci a los heteroarenos básicos.
Lograr el control simultáneo de la enantioselectividad y la regioselectividad.
Para permitir una síntesis eficiente de bloques de construcción de moléculas pequeñas enriquecidas con enantio.

Principales métodos:

Radicales procirales utilizados generados a partir de derivados de aminoácidos.
Se empleó un catalizador de ácido de Brønsted quiral enantiopuro para la activación del sustrato y la inducción de la asimetría.
Incorpora un fotocatalizador de iridio para mediar en los procesos de transferencia de electrones.

Principales resultados:

Se ha demostrado un excelente control tanto de la enantioselectividad como de la regioselectividad en adiciones de radicales.
Se aplicó con éxito el método a las piridinas y las quinolinas.
Bloques de construcción de moléculas pequeñas enriquecidas con enantio con motivos heterocíclicos básicos.

Conclusiones:

El método desarrollado proporciona una herramienta poderosa para la síntesis asimétrica de compuestos heterocíclicos valiosos.
Este enfoque avanza significativamente la capacidad de controlar la estereoquímica en las reacciones de tipo Minisci.
Anticipado para acelerar el descubrimiento y desarrollo de nuevos productos farmacéuticos.

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