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Apertura del anillo/fragmentación de dihidropironas para la síntesis de alcoholes de homopropargilo

Jumreang Tummatorn¹, Gregory B Dudley

¹Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA.

Journal of the American Chemical Society

|March 25, 2008

Resumen

La adición de metil Grignard a los triflados de 5,6-dihidro-2-pirona desencadena la apertura estereospecífica del anillo y la escisión del enlace C-C. Esta reacción ofrece un método sencillo para sintetizar alcoholes quirales de homopropargil a través de la extrusión de carbonilo.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química sintética de la química sintética.

Sus antecedentes:

Los triflados de 5,6-dihidro-2-pirona (DHP) son unos versátiles intermedios sintéticos.
Los alcoholes quirales homopropargil son bloques de construcción valiosos en la síntesis orgánica.

Objetivo del estudio:

Para investigar la reacción del metil Grignard con los triflados de DHP.
Desarrollar una estrategia unificada para la síntesis de alcoholes quirales homopropargyl.

Principales métodos:

Adición nucleofílica de metil Grignard a los triflados de DHP.
Reacciones estereospecíficas de apertura de anillos y de escisión de enlaces C-C.
Extrusión de carbonilo. extrusión de carbonilo.

Principales resultados:

La reacción procede estereospecíficamente, conservando la estereocímica de los triflados de DHP iniciales.
Los alcoholes de homopropargilo se proporcionan de manera eficiente.
Se establece una estrategia unificada y operacionalmente simple.

Conclusiones:

La adición nucleofílica de metil Grignard a los triflados de DHP es un método eficaz para generar alcoholes de homopropargilo.
Este enfoque proporciona una nueva ruta a los alcoholes quirales homopropargyl.

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