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Reorganización de los derivados de pineno hidroxilados en marcos de tipo fenchone: evidencia computacional para la

Marcus Blümel¹, Shota Nagasawa¹, Katherine Blackford¹

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

Journal of the American Chemical Society

|July 4, 2018

Resumen

Una nueva reacción catalizada por ácido crea eficientemente estructuras complejas de tipo fenclónico a partir de derivados de pineno hidroxilados. Este método ofrece altos rendimientos y selectividad, controlados por un mecanismo de bifurcación de estado post-transición único.

Área de la Ciencia:

Química orgánica
Mecanismo de reacción
Síntesis estereoselectiva

Sus antecedentes:

Los derivados del pineno son productos naturales valiosos.
El desarrollo de rutas sintéticas eficientes para andamios complejos es crucial.
La comprensión de los mecanismos de reacción guía la estrategia sintética.

Objetivo del estudio:

Desarrollar una nueva reacción en cascada para sintetizar andamios tricíclicos de tipo fencona.
Investigar el mecanismo y la selectividad de la reacción.
Explorar el papel de las percepciones químicas cuánticas en el control de la estereoselectividad.

Principales métodos:

Reacción en cascada de reordenamiento de Prins y semipinacol catalizada por el ácido.
Se utilizan derivados de pineno hidroxilados como materiales de partida.
Se empleó el análisis químico cuántico para estudiar el estado de transición.

Principales resultados:

Se obtiene un rendimiento muy alto y una diastereoselectividad para andamios de tipo fenchone.
Identificamos una superficie de energía potencial extremadamente plana alrededor del estado de transición.
Control dinámico demostrado a través de la bifurcación del estado de transición posterior (PTSB) que favorece al fenchone sobre los esqueletos de bornil.

Conclusiones:

Se ha establecido una vía sintética novedosa y eficiente para los andamios de tipo fenchone.
El análisis químico cuántico proporciona una comprensión mecanicista crítica de la selectividad.
El mecanismo PTSB ofrece un nuevo paradigma para controlar los resultados estereoquímicos en reacciones complejas.

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