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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
Published on: January 17, 2020
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Enantioselectiva meta-C-H arilación remota y alquilación a través de un mediador transitorio quiral
Hang Shi1, Alastair N Herron1, Ying Shao1
1Department of Chemistry, The Scripps Research Institute, La Jolla, CA, USA.
Nature
|June 20, 2018
Resumen
Los investigadores desarrollaron un nuevo método para la activación remota de C-H enantioselectiva utilizando un mediador quiral de norborneno. Esta estrategia permite la funcionalización asimétrica de los meta enlaces C-H desafiantes en las moléculas.
Área de la Ciencia:
- Química orgánica
- Catálisis asimétrica
Sus antecedentes:
- La activación enantioselectiva de carbono-hidrógeno (C-H) es crucial para sintetizar moléculas quirales.
- Los métodos actuales se limitan a formar metaciclos de cinco o seis miembros, lo que restringe la funcionalidad de los enlaces C-H remotos.
Objetivo del estudio:
- Desarrollar una nueva estrategia para la activación remota de C-H enantioselectiva.
- Permitir la funcionalidad asimétrica de los meta enlaces C-H, superando las limitaciones de los métodos existentes.
Principales métodos:
- Utilizó un norborneno quiral como mediador transitorio para transmitir la activación de C-H desde las posiciones orto a meta.
- Se aplicó la estrategia a la arilación meta-C-H enantioselectiva de las benzilaminas y a la arilación/alquilación de las homobenzilaminas.
Principales resultados:
- Se ha logrado la activación y funcionalización enantioselectiva del meta-C-H utilizando la estrategia del mediador transitorio.
- Se han demostrado enantioselectividades comparables en varios sustratos con grupos coordinadores σ-donantes neutros o aniónicos.
Conclusiones:
- La estrategia de relé desarrollada ofrece un nuevo enfoque para la inducción quiral remota en catálisis asimétrica.
- Este método expande el alcance de la activación C-H para la construcción de moléculas quirales complejas.
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