Organocatalytic Strategies to Stereoselectively Trap Photochemically Generated Hydroxy-o-quinodimethanes
Light excitation of ortho-alkyl aromatic ketones and aldehydes enables access to hydroxy-o-quinodimethanes. These reactive electron-rich intermediates are sufficiently long-lived to productively engage in chemical processes, mainly acting as dienes in [4+2]-cycloadditions with electron-poor alkenes....
| Autores: | , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2018 |
| 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:2072/335531 |
| Acceso en línea: | http://hdl.handle.net/2072/335531 https://doi.org/10.1002/ejoc.201800081 |
| Access Level: | acceso abierto |
| Palabra clave: | 54 |
| Sumario: | Light excitation of ortho-alkyl aromatic ketones and aldehydes enables access to hydroxy-o-quinodimethanes. These reactive electron-rich intermediates are sufficiently long-lived to productively engage in chemical processes, mainly acting as dienes in [4+2]-cycloadditions with electron-poor alkenes. Since the early discovery of this photoenolization mechanism, which dates back to 1961, a variety of transformations has been developed, providing a photochemical alternative to classical Diels-Alder chemistry. However, enantioselective catalytic versions of the photenoliza tion/Diels-Alder sequence have remained elusive until recently. This review describes how the field of enantioselective organocatalysis has provided suitable tools to stereoselectively trap photochemically generated hydroxy-o-quinodimethanes. Recent studies also demonstrated that the chemistry is not limited to cycloaddition-type manifolds, but it can be expanded to develop intermolecular enantioselective addition processes. |
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