Photochemical Organocatalytic Regio- and Enantioselective Conjugate Addition of Allyl Groups to Enals
We report the first catalytic enantioselective conjugate addition of allyl groups to a,b-unsaturated aldehydes. The chemistry exploits the visible-light-excitation of chiral iminium ions to activate allyl silanes towards the formation of allylic radicals, which are then intercepted stereoselectively...
| Autores: | , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2021 |
| País: | España |
| Institución: | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| Repositorio: | Recercat. Dipósit de la Recerca de Catalunya |
| OAI Identifier: | oai:recercat.cat:2072/520867 |
| Acceso en línea: | http://hdl.handle.net/2072/520867 https://doi.org/10.1002/anie.202111648 |
| Access Level: | acceso abierto |
| Palabra clave: | 54 |
| Sumario: | We report the first catalytic enantioselective conjugate addition of allyl groups to a,b-unsaturated aldehydes. The chemistry exploits the visible-light-excitation of chiral iminium ions to activate allyl silanes towards the formation of allylic radicals, which are then intercepted stereoselectively. The underlying radical mechanism of this process overcomes the poor regio- and chemoselectivity that traditionally affects the conjugate allylation of enals proceeding via polar pathways. We also demonstrate how this organocatalytic strategy could selectively install a valuable prenyl fragment at the b-carbon of enals. |
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