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Fluorolectonización asimétrica con un catalizador bifuncional de hidroxilo carboxilato

Hiromichi Egami¹, Junshi Asada¹, Kentaro Sato¹

¹†School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.

Journal of the American Chemical Society

|August 8, 2015

Resumen

Este estudio introduce un nuevo organocatalisador bifuncional para la fluoroelectonización altamente enantioselectiva utilizando Selectfluor. Este método produce eficientemente isobenzofuranonas fluoradas con un excelente control estéreo.

Área de la Ciencia:

Química orgánica
Síntesis asimétrica
La catálisis orgánica

Sus antecedentes:

La fluoroelectonización enantioselectiva es crucial para la síntesis de compuestos fluorados quirales.
El desarrollo de sistemas catalíticos eficientes y selectivos sigue siendo un desafío.

Objetivo del estudio:

Informar sobre la primera fluorolactonización altamente enantioselectiva mediante el uso de un reactivo fluorado electrófilo y un nuevo organocatalisador.
Explorar el mecanismo y las aplicaciones potenciales de este nuevo sistema catalítico.

Principales métodos:

Se utiliza el Selectfluor como reactivo fluorante electrófilo.
Se utilizó un nuevo organocatalisador bifuncional con un anión carboxilato y una unidad de alcohol bencílico.
Se han realizado estudios mecanicistas para elucidar la vía de reacción.

Principales resultados:

Se ha logrado una fluoroelectonización altamente enantioselectiva, dando lugar a isobenzofuranonas fluoradas.
Productos obtenidos en buenos rendimientos con un exceso enantiomérico (ee) de hasta el 94% y una relación enantiomérica (er) de 97:3.

Conclusiones:

Se ha demostrado la primera fluoroelectonización altamente enantioselectiva con Selectfluor y un nuevo organocatalisador bifuncional.
Propuso un mecanismo de reacción único con potencial para aplicaciones más amplias en la síntesis orgánica.

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