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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 21, 2014
Catálisis secuencial Ru-Pd: un protocolo de dos catalizadores y una olla para la síntesis de N- y O-heterociclos
Barry M Trost1, Michelle R Machacek, Brian D Faulk
1Department of Chemistry, Stanford University, Stanford, California 94305, USA. bmtrost@stanford.edu
Journal of the American Chemical Society
|May 18, 2006
Resumen
Una nueva síntesis de dos metales y una olla crea eficientemente heterociclos N y O puros. Este método versátil permite el acceso a diastereómeros difíciles y intermedios útiles para la síntesis de moléculas complejas.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química sintética de la química sintética.
- La catálisis por catálisis.
Sus antecedentes:
- El desarrollo de rutas sintéticas eficientes y selectivas para compuestos heterocíclicos complejos es crucial en la química orgánica.
- Los métodos tradicionales de ciclización a menudo se enfrentan a desafíos para acceder a diastereómeros específicos debido a las limitaciones termodinámicas.
Objetivo del estudio:
- Desarrollar una síntesis práctica, atómica y selectiva de dos metales y una olla para los heterociclos N- y O enantio y diastereopuros.
- Para permitir la síntesis de diastereómeros difíciles, incluidos los termodinámicamente desfavorecidos.
- Demostrar la utilidad de los heterociclos sintetizados como intermedios en la síntesis total.
Principales métodos:
- Se empleó una estrategia de reacción de dos metales y una olla para la síntesis de heterociclos.
- La catálisis quiral se utilizó para controlar la estereoquímica y acceder a todos los diastereómeros posibles.
- La química del Z-vinilsilano se utilizó para generar olefinas trísubstituidas estereodefinidas.
Principales resultados:
- El método desarrollado produce eficientemente productos heterocíclicos enantio- y diastereopuros N- y O.
- La síntesis permite la formación de todos los diastereómeros, superando las barreras termodinámicas.
- La naturaleza del control estereoquímico varía entre los nucleófilos de aminas y alcoholes.
- Se accedió a intermedios heterocíclicos sintéticamente valiosos y a olefinas trísubstituidas estereodefinidas.
Conclusiones:
- La síntesis de dos metales y una olla ofrece un enfoque muy práctico y versátil para heterociclos complejos.
- El método proporciona acceso a estereoisómeros previamente difíciles de obtener.
- Los heterociclos sintetizados sirven como intermediarios clave en la síntesis total de moléculas biológicamente relevantes, incluidos los compuestos farmacéuticos.
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