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Reacciones de aldol descarboxilativas de los ésteres beta-ceto de alilo a través de la catálisis heterobimetálica

Sha Lou¹, John A Westbrook, Scott E Schaus

¹Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA.

Journal of the American Chemical Society

|September 16, 2004

Resumen

Se lograron reacciones de aldol descarboxilativas leves y selectivas utilizando catálisis heterobimetálica. Los complejos de paladio (Pd) e iterbio (Yb) promueven la formación de enolados cetónicos a partir de ésteres beta-ceto de alilo para su adición a los aldehídos.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.

Sus antecedentes:

Las reacciones descarboxilativas de aldol ofrecen una vía para la formación de enlaces carbono-carbono.
Los ésteres beta-ceto de alilo son materiales de partida versátiles en la síntesis orgánica.

Objetivo del estudio:

Desarrollar un método suave y selectivo para las reacciones aldoles descarboxilativas.
Para explorar la utilidad de la catálisis heterobimetálica en esta transformación.

Principales métodos:

Se utilizan complejos de paladio (Pd(0) e iterbio (Yb(III)) con ligandos DIOP.
Reacciones realizadas a temperatura ambiente.
Generación in situ de enolados cetónicos a partir de ésteres beta-ceto de alilo.

Principales resultados:

Se lograron reacciones aldólicas descarboxilativas ligeras y selectivas catalizadas heterobimetálicamente.
Demostró la necesidad tanto de Pd como de Yb para optimizar las condiciones de reacción.
Los enolados cetónicos acoplados con éxito con aldehídos.

Conclusiones:

Desarrolló un nuevo sistema catalítico heterobimetálico para reacciones aldoles descarboxilativas.
Destacó el efecto sinérgico de Pd e Yb en la promoción de la reacción.
Estableció una nueva ruta sintética utilizando ésteres beta-ceto de alilo.

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