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Síntesis de estereocentros cuaternarios adyacentes por aliboración asimétrica catalítica

Rauful Alam¹, Tobias Vollgraff¹, Lars Eriksson¹

¹Department of Organic Chemistry and ‡Department of Materials and Environmental Chemistry, Stockholm University , SE-106 91 Stockholm, Sweden.

Journal of the American Chemical Society

|August 29, 2015

Resumen

Los catalizadores quirales permiten la síntesis estereoselectiva de estereocentros cuaternarios adyacentes a través de la aliboración. Este método ofrece un control preciso de la estereo- y enantioselectividad en un solo paso.

Área de la Ciencia:

Química orgánica
Síntesis asimétrica

Sus antecedentes:

Los estereocentros cuaternarios son motivos cruciales en muchos productos naturales y farmacéuticos.
El desarrollo de métodos eficientes para su síntesis asimétrica sigue siendo un desafío importante en la química orgánica.

Objetivo del estudio:

Desarrollar un método altamente selectivo para la construcción de estereocentros cuaternarios adyacentes.
Lograr un control total de la estereo- y enantioselectividad en las reacciones de aliboración.

Principales métodos:

Aliboración de cetonas mediante el uso de ácidos aliborónicos disueltos γ.
El uso de derivados quirales de BINOL como catalizadores para inducir la asimetría.

Principales resultados:

Síntesis exitosa en un solo paso de estereocentros cuaternarios adyacentes con alta selectividad.
Capacidad demostrada para lograr un control estereo y enantio completo mediante la optimización del catalizador y el sustrato quirales.

Conclusiones:

La aliboración catalizada por quiral BINOL proporciona una ruta eficaz hacia los estereocentros complejos.
Esta metodología ofrece una herramienta poderosa para la síntesis asimétrica, lo que permite un control preciso de los resultados estereochemical.

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