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Isomerización enantioselectiva catalizada por el rodio de los alcoholes alelicos secundarios

Tang-Lin Liu¹, Teng Wei Ng¹, Yu Zhao¹

¹Department of Chemistry, National University of Singapore , 3 Science Drive 3, Republic of Singapore 117543.

Journal of the American Chemical Society

|March 2, 2017

Resumen

Este estudio introduce la primera isomerización catalítica enantioselectiva de los alcoholes alílicos, creando cetonas quirales valiosas. El método convierte eficientemente los alcoholes racémicos en productos enriquecidos con enantio en condiciones suaves.

Área de la Ciencia:

Química orgánica
Síntesis estereoselectiva

Sus antecedentes:

Las cetonas quirales con estereocentros α-terciarios son bloques de construcción importantes.
Los métodos existentes para sintetizar estos compuestos pueden ser limitados en alcance o eficiencia.

Objetivo del estudio:

Desarrollar un nuevo método catalítico enantioselectivo para la isomerización de alcoholes alelicos secundarios.
Para acceder a las cetonas con un estereocentro α-terciario.

Principales métodos:

Se utilizaron catalizadores disponibles en el mercado para la reacción de isomerización.
Se emplean condiciones de reacción suaves para garantizar la compatibilidad del sustrato.

Principales resultados:

Logró la primera isomerización enantioselectiva catalítica de alcoholes alelicos secundarios a cetonas.
Se ha demostrado la conversión estereoconvergente de sustratos racémicos en productos enriquecidos con enantio.
El método proporciona acceso a las cetonas con un estereocentro α-terciario.

Conclusiones:

Este nuevo método ofrece una ruta atractiva y eficiente para la síntesis estereoselectiva.
El uso de catalizadores fácilmente disponibles y condiciones suaves mejora su practicidad.

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