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La estrategia del grupo cooperativo remoto permite los ligandos para la catálisis asimétrica acelerada del oro

Zhixun Wang¹, Corrado Nicolini², Cedric Hervieu¹

¹Department of Chemistry & Biochemistry, University of California, Santa Barbara , Santa Barbara, California 93106, United States.

Journal of the American Chemical Society

|October 24, 2017

Resumen

Este estudio introduce la catálisis acelerada asimétrica del oro utilizando un nuevo ligando quiral. Este método logra una alta enantioselectividad y permite bajas cargas de catalizador, permitiendo el acceso a los cuatro estereoisómeros de 2-viniltetrahidrofuranos.

Área de la Ciencia:

Química orgánica
Catálisis
Síntesis asimétrica

Sus antecedentes:

La catálisis asimétrica del oro es crucial para sintetizar moléculas quirales.
Los métodos existentes a menudo se basan en el impedimento estérico desacelerado, lo que limita la eficiencia.
Existe la necesidad de nuevas estrategias aceleradoras en la catálisis asimétrica del oro.

Objetivo del estudio:

Para desarrollar un nuevo acelerador asimétrico de catálisis de oro.
Para lograr una alta enantioselectividad en la ciclización de 4-aleno-1-ols.
Para permitir la síntesis de los cuatro estereoisómeros de los 2-viniltetrahidrofuranos.

Principales métodos:

Diseño de un ligando quiral basado en binaftil con un grupo de amida remoto.
Utilizando la cooperación quiral ligando-metal para la catálisis.
Emplear el ligando como catalizador de base general para acelerar la ciclización.

Principales resultados:

Logró la primera catálisis aceleradora asimétrica de oro a través de la cooperación quiral ligando-metal.
Se ha demostrado una alta enantioselectividad con sustratos achirales y una selectividad mantenida con sustratos quirales.
Acceso habilitado a los cuatro estereoisómeros de 2-viniltetrahidrofuranos con alta selectividad utilizando bajas cargas de catalizador (100 ppm).

Conclusiones:

El nuevo diseño del ligando permite una estrategia aceleradora para la catálisis asimétrica del oro.
Este enfoque ofrece un método distintivo y eficiente para sintetizar tetrahidrofuranos quirales.
Los hallazgos presentan un nuevo paradigma en la catálisis asimétrica, que va más allá del obstáculo estérico.

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