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El fosfato de diariodonio quiral permite la acetalización diastereoelectiva impulsada por la luz α-C ((sp³)

Baihua Ye¹, Jie Zhao¹, Ke Zhao¹

¹Department of Chemistry , University of California , Berkeley , California 94720 , United States.

Journal of the American Chemical Society

|June 26, 2018

Resumen

Este estudio introduce un nuevo método para la funcionalización estereoselectiva del enlace C ((sp3) -H en éteres cíclicos. Este enfoque permite un control preciso de la complejidad molecular y la creación de compuestos enantiopuros.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

La funcionalización del enlace C ((sp3) -H es clave para la construcción de moléculas complejas.
La síntesis asimétrica es crucial para acceder a los compuestos enantiopuros.
Los éteres cíclicos son motivos estructurales importantes en muchas moléculas.

Objetivo del estudio:

Desarrollar un método estereoselectivo para la funcionalización de enlaces C ((sp3) -H en éteres cíclicos.
Para lograr el control regio- y estereoquímico en las reacciones de acetalización.
Para permitir la síntesis de materiales enantiopuros y ricos en sp3.

Principales métodos:

Utilizó una sal de diaryliodonium fotoquímicamente activa.
Empleado un catalizador de transferencia de fase aniónica.
Aplicó el método a la acetalización α-C-H de furanos y piranos con nucleófilos de alcohol.

Principales resultados:

Se logró la funcionalización estereoselectiva de los enlaces C ((sp3) -H en éteres cíclicos.
Se ha demostrado el control regio- y estereoquímico en la acetalización de furanos y piranos.
Controlado con éxito la configuración en el carbono acetal exocíclico.

Conclusiones:

El método desarrollado ofrece una poderosa estrategia para la funcionalización asimétrica C ((sp3) -H.
Este trabajo proporciona acceso a derivados de éter cíclico ricos en enantiopuro sp3.
La metodología permite un control preciso de la estereoquímica en la síntesis de moléculas complejas.

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