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Hidrogenación enantioselectiva de 3-alquilidenelactamas: el cribado de alto rendimiento proporciona una solución

Tai-Yuen Yue¹, William A Nugent

¹Bristol-Myers Squibb Company, Process Research and Development Department, Chambers Works, P.O. Box 269, Deepwater, New Jersey 08023-0269, USA.

Journal of the American Chemical Society

|November 15, 2002

Resumen

Un nuevo catalizador de iridio, BF4, cataliza de manera eficiente la hidrogenación enantioselectiva de los 3-alquilidenelactamos. Este avance ofrece un método general para sintetizar valiosos compuestos de lactamo.

Área de la Ciencia:

La catálisis de la catálisis.
Química orgánica es la química orgánica.
Síntesis asimétrica de síntesis.

Sus antecedentes:

El desarrollo de catalizadores eficientes para la hidrogenación asimétrica es crucial en la síntesis orgánica.
Los 3-alquilidinelactamas son importantes intermediarios sintéticos. también conocidos como 3-alquilidinelactamas.
Los catalizadores anteriores mostraron un éxito limitado con ligandos flexibles como el BDPP.

Objetivo del estudio:

Para identificar nuevos catalizadores para la hidrogenación enantioselectiva de los 3-alquilidenelactamos.
Explorar el alcance y la escalabilidad del sistema catalítico identificado.

Principales métodos:

Cribado de alto rendimiento de 256 combinaciones de catalizadores (8 precursores metálicos x 32 ligandos de fosfina).
Evaluación de [[[BDPP]]Ir[[COD]]]BF4 para la hidrogenación asimétrica de varios lactamos.
Estudio a gran escala del proceso de hidrogenación.

Principales resultados:

Identificación de [[[BDPP]]Ir[[COD]]]BF4 como un catalizador muy eficaz para la hidrogenación enantioselectiva de los 3-alquilidenelactamas.
El catalizador demostró una amplia aplicabilidad a las lactamas de cinco y seis miembros.
Aumento exitoso de la escala de la reacción a un nivel de 20 kg.

Conclusiones:

BF4 es un catalizador sorprendente pero eficaz para la síntesis asimétrica de lactamo.
El método desarrollado proporciona una ruta escalable a los lactamos enriquecidos enantioméricamente.
Este hallazgo amplía la utilidad de la catálisis del iridio en la síntesis orgánica.

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