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Síntesis y aplicaciones de los biciclo[1.1.0]butanos polisustituidos

Ryan E McNamee¹, Amber L Thompson¹, Edward A Anderson¹

¹Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, U.K.

Journal of the American Chemical Society

|December 14, 2021

Resumen

Desarrollamos un nuevo método para sintetizar biciclo[1.1.0]butanos sustituidos (BCB) utilizando la metalización dirigida. Este enfoque permite la funcionalidad en etapa tardía, creando diversos bloques de construcción de BCB y ofreciendo nuevos conocimientos sobre la formación de biciclo[1.1.1]pentano.

Área de la Ciencia:

Química orgánica
Metodología sintética
Síntesis de liberación de tensión

Sus antecedentes:

Los biciclo[1.1.0]butanos (BCB) son intermediarios clave en la síntesis de anillos polisustituidos de cuatro miembros.
Los métodos actuales para la funcionalización de BCB son limitados, a menudo requieren síntesis lineales con alcance restringido.

Objetivo del estudio:

Desarrollar un método versátil y eficiente para sintetizar BCBs sustituidos.
Ampliar el alcance de la funcionalidad de los andamios BCB.
Investigar el mecanismo de inserción del dihalocarbeno en los BCB.

Principales métodos:

Metalización dirigida de las amidas de biciclo[1.1.0]butano.
Funcionalización de la etapa tardía del andamio BCB.
Síntesis de BCB monodeutrado para estudios mecanicistas.

Principales resultados:

Se han sintetizado con éxito BCBs tri y tetrasubstituidos.
Demostró un enfoque sencillo en las últimas etapas para diversos derivados BCB.
Obtuvo conocimientos mecanicistas sobre la formación de biciclo[1.1.1]pentano a través de la inserción de dihalocarbenos.

Conclusiones:

La metalización dirigida de las amidas de BCB proporciona una nueva vía poderosa para los BCB sustituidos.
Este método ofrece una plataforma versátil para generar valiosos bloques de construcción de anillos pequeños.
Los estudios mecánicos con BCB deuterados aclararon aspectos clave de las reacciones de inserción de carbenos.

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