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Síntesis asimétrica organocatalizadora de éteres silílicos estereogénicos

Hui Zhou¹, Jung Tae Han¹, Nils Nöthling¹

¹Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.

Journal of the American Chemical Society

|June 1, 2022

Resumen

Los investigadores desarrollaron un nuevo método para crear organosilanos quirales utilizando organocatálisis. Este avance proporciona éteres silílicos enantiopuros, valiosos para diversas aplicaciones químicas.

Área de la Ciencia:

Química del silicio orgánico
Catálisis asimétrica
Síntesis orgánica

Sus antecedentes:

Los organosilanos enantiopuros son intermediarios sintéticos muy importantes.
Los métodos existentes para la síntesis asimétrica de estos compuestos son limitados.

Objetivo del estudio:

Informar sobre la primera síntesis organocatalítica enantioselectiva de éteres silílicos quirales terciarios centrados en el silicio.
Para establecer una nueva reacción de desimetrización para crear valiosos compuestos quirales de silicio.

Principales métodos:

Se utilizaron catalizadores de imidodifosforimidato (IDPi) desarrollados recientemente.
Se empleó una reacción de intercambio de silicio-hidrógeno desimetrizada entre bis (metil) silanos y fenoles.

Principales resultados:

Se obtienen altos rendimientos y excelentes quimioselectividades y enantioselectividades para varios éteres silílicos enantiopuros.
Demostró la fácil derivación de los éteres de silicio obtenidos en otros compuestos quirales de silicio.

Conclusiones:

El método desarrollado ofrece un avance significativo en la síntesis asimétrica de organosilanos.
Los éteres silílicos quirales resultantes sirven como precursores versátiles para diversos materiales y moléculas basados en silicio quiral.

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