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Resolución cinética del alcohol alílico con alcóxidos basados en quiral BINOL: una combinación de estudios
Yidong Liu, Song Liu, Dongmei Li
1Department of Chemistry , Sungkyunkwan University , 2066, Seobu-ro , Jangan-gu, Suwon , Gyeonggi 440-746 , Korea.
Journal of the American Chemical Society
|December 19, 2018
Resumen
Este estudio introduce un nuevo método sin metales de transición para la creación de alcoholes alelicos secundarios quirales utilizando catalizadores derivados de BINOL. Esta isomerización enantioselectiva ofrece altos rendimientos y selectividad, con aplicaciones en la síntesis de productos naturales.
Área de la Ciencia:
- Química orgánica
- Catálisis asimétrica
Sus antecedentes:
- Los alcoholes alelicos secundarios quirales son valiosos intermediarios sintéticos.
- Los métodos existentes a menudo se basan en metales de transición o carecen de una alta enantioselectividad.
Objetivo del estudio:
- Desarrollar una resolución cinética catalítica enantioselectiva y libre de metales de transición de los alcoholes alílicos.
- Para sintetizar alcoholes alelicos secundarios quirales con alto exceso enantiomérico (ee) y selectividad.
Principales métodos:
- Síntesis de alcóxidos basados en derivados quirales de BINOL.
- Isomerización asimétrica catalizada por catalizadores de base de Brønsted bifuncionales.
- Estudios mecánicos para identificar las especies activas y las vías de reacción.
Principales resultados:
- Identificó un prometedor catalizador quiral de base de Brønsted derivado del BINOL.
- Se obtiene una elevada enantioselectividad (hasta el 99% ee) y selectividad (factor S > 200).
- Se ha demostrado la eficacia del catalizador en la síntesis del producto natural (+) -veraguensin.
Conclusiones:
- Este trabajo presenta la primera isomerización catalizada con base libre de metales de transición para sintetizar alcoholes alelicos secundarios quirales.
- El grupo fenol de BINOL juega un papel crucial en la reactividad y enantioselectividad a través de enlaces de hidrógeno.
- La estrategia desarrollada es aplicable a la síntesis de moléculas bioactivas complejas.
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