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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

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Versátil síntesis enantioselectiva de lactonas funcionalizadas a través de la oxitofuncionalización radical

Rong Zhu¹, Stephen L Buchwald¹

¹Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.

Journal of the American Chemical Society

|June 13, 2015

Resumen

Un nuevo método catalizado por el cobre sintetiza rápidamente lactonas enriquecidas enantioméricamente. Esta estrategia versátil crea bloques de construcción quirales con centros estereogénicos tetrasubstituidos desafiantes.

Área de la Ciencia:

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

Sus antecedentes:

Las lactonas son motivos estructurales cruciales en productos naturales y productos farmacéuticos.
El acceso a las lactonas enantioméricamente enriquecidas, especialmente aquellas con estereocentros altamente sustituidos, sigue siendo un desafío sintético.

Objetivo del estudio:

Desarrollar un método versátil y rápido para sintetizar diversas lactonas enriquecidas enantioméricamente.
Para establecer una estrategia de oxifunzionalización de radicales enantioselectivos catalizados por cobre para los alquenos.

Principales métodos:

Empleando la catálisis del cobre para la oxitofuncionalización radical enantioselectiva de los alquenos.
Implementando una serie de reacciones de difuncionalización que incluyen oxidación, oxisulfonilación, oxirilación, diacilosilación y oxilación.

Principales resultados:

Demostró un método versátil para la síntesis rápida de lactonas enriquecidas enantioméricamente.
Se logró un acceso directo a los bloques de construcción de la lactona quiral con centros estereogénicos tetrasubstituidos.
Demostró la utilidad de la oxitofuncionalización de radicales enantioselectivos catalizados por cobre.

Conclusiones:

El método desarrollado ofrece un enfoque poderoso para sintetizar valiosos bloques de construcción de lactona quiral.
Esta estrategia supera las limitaciones tradicionales en el acceso a estructuras complejas de lactona.
La metodología proporciona un amplio alcance para crear diversas lactonas enriquecidas enantioméricamente.

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