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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
La carbosulfenilación catalítica, enantioselectiva y intramolecular de las olefinas
1Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. sdenmark@illinois.edu
Journal of the American Chemical Society
|April 20, 2013
Resumen
Este estudio introduce la primera carbosulfenilación catalítica enantioselectiva de alquenos utilizando un nuevo catalizador de selenofosforamida. El método produce de manera eficiente tetrahidronaftalenos quirales con alta estereoselectividad.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- La catálisis de la catálisis.
- Síntesis asimétrica de síntesis.
Sus antecedentes:
- Las reacciones de carbosulfenilación son cruciales para la formación de enlaces carbono-azufre.
- Los métodos enantioselectivos son esenciales para la síntesis de moléculas quirales.
Objetivo del estudio:
- Desarrollar la primera carbosulfenilación catalítica y enantioselectiva de alquenos utilizando un nucleófilo aromático.
- Para explorar la utilidad de un catalizador de selenofosforamida basado en BINAM en esta transformación.
Principales métodos:
- Utilizó un catalizador de selenofosforamida basado en BINAM.
- Los alquenos E-alquilo y arilo sustituidos empleados como sustratos.
- Investigó el mecanismo de reacción y los resultados estereoquímicos.
Principales resultados:
- Logró la primera carbosulfenilación catalítica y enantioselectiva de alquenos.
- Se obtienen productos de tetrahidronaftaleno con una completa diastereospecificidad.
- Se ha demostrado que las relaciones enantioméricas son generalmente altas para los productos.
Conclusiones:
- El método desarrollado proporciona una ruta eficiente a los tetrahidronaftalenos quirales.
- El catalizador de selenofosforamida basado en BINAM es eficaz para la carbosulfenilación enantioselectiva.
- Este trabajo amplía el alcance de la catálisis asimétrica para la formación de enlaces C-S.
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