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Síntesis telescópica de ésteres glicídicos 2-arílicos a partir de aldehídos impulsada por serendipia

Vincenzo Battaglia¹, Isaac G Sonsona¹, Sara Meninno¹

¹Dipartimento di Chimica e Biologia "A. Zambelli", Università di Salerno, Via Giovanni Paolo II 132, 84084 Fisciano, Italy.

Organic letters

|January 19, 2026

Resumen

Un nuevo método de síntesis de un solo paso crea valiosos ésteres etílicos de 2-(hetero)aril glicídicos a partir de aldehídos. Este enfoque práctico produce epóxidos de manera eficiente, ofreciendo una nueva ruta hacia moléculas complejas.

Área de la Ciencia:

Síntesis Orgánica
Catálisis
Química Verde

Sus antecedentes:

El desarrollo de rutas sintéticas eficientes para moléculas orgánicas complejas es crucial.
Los ésteres etílicos de 2-(hetero)aril glicídicos son intermedios sintéticos valiosos.
Los métodos existentes pueden carecer de generalidad, practicidad o emplear condiciones duras.

Objetivo del estudio:

Establecer un método general y práctico para la síntesis de ésteres etílicos de 2-(hetero)aril glicídicos.
Desarrollar un protocolo de un solo paso que sea eficiente y escalable.
Explorar la utilidad de los epóxidos sintetizados para su posterior elaboración.

Principales métodos:

Se empleó una secuencia telescópica de tres pasos y siete reacciones.
La secuencia implicó condensación de Knoevenagel, adición de nitro-Michael, hidroxilación, doble eliminación, epoxidación y esterificación.
Se utilizaron reactivos disponibles comercialmente, un catalizador y aldehídos como materias primas.

Principales resultados:

Se desarrolló un método general y práctico para la síntesis de ésteres etílicos de 2-(hetero)aril glicídicos.
El protocolo de un solo paso logró hasta un 73% de rendimiento general de epóxidos.
El proceso opera a temperatura ambiente en disolventes benignos y es escalable a 5 mmol.

Conclusiones:

El método desarrollado proporciona una ruta fácil y eficiente hacia epóxidos valiosos.
Los epóxidos sintetizados pueden transformarse posteriormente en ésteres de β-amino α-hidroxi con estereocentros cuaternarios.
Este protocolo ofrece un enfoque sostenible y práctico para acceder a arquitecturas moleculares complejas.

Palabras clave:

síntesis de un solo paso ésteres glicídicos aldehídos epóxidos química orgánica síntesis telescópica

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