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Fotocatalítico enantioselectivo [3 + 2] Cicloadiciones de las cetonas de arilo ciclopropilo

Adrian G Amador¹, Evan M Sherbrook¹, Tehshik P Yoon¹

¹Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.

Journal of the American Chemical Society

|March 26, 2016

Resumen

Este estudio introduce un nuevo método catalítico para reacciones de fotocicloadición asimétricas [3 + 2], permitiendo la síntesis enantiocontrolada de estructuras complejas de ciclopentano. Esto hace avanzar la química de la cicloadición fotoquímica para los químicos sintéticos.

Área de la Ciencia:

Química orgánica
La fotoquímica
Catálisis asimétrica

Sus antecedentes:

El control estereoquímico en reacciones de fotocicloadición es un desafío.
Los métodos catalíticos existentes se centran principalmente en las adiciones fotociclo [2 + 2] de enonas.

Objetivo del estudio:

Desarrollar un método para la fotocicloadición asimétrica [3 + 2] de las cetonas de arilo ciclopropilo.
Para permitir la síntesis controlada por enantio de estructuras de ciclopentano densamente sustituidas.

Principales métodos:

Utilizó una estrategia de doble catalizador.
Reacciones de fotocicloadición empleadas con las cetonas de arilo ciclopropilo.

Principales resultados:

Se ha logrado la construcción enantio-controlada de estructuras complejas de ciclopentano.
Se ha demostrado una nueva vía de fotocicloadición asimétrica [3 + 2].
Estructuras sintetizadas no accesibles mediante otros métodos catalíticos.

Conclusiones:

La estrategia de doble catalizador desarrollada amplía el acceso a las cicloadiciones fotoquímicas enantioselectivas.
Este método amplía el alcance de las reacciones de cicloadición fotoquímicas factibles.

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