Photoredox Organocatalysis for the Enantioselective Synthesis of 1,7- Dicarbonyl Compounds
We describe an asymmetric organocatalytic method to synthesize 1,7-dicarbonyl compounds containing a β-stereocenter. The chemistry relies on the formation of γ-keto radicals, generated upon oxidative ring-opening of cyclobutanols mastered by an organic photoredox catalyst. These non-stabilized prima...
| Autores: | , , , |
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| Formato: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2022 |
| País: | España |
| Recursos: | 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:2072/522241 |
| Acesso em linha: | http://hdl.handle.net/2072/522241 https://doi.org/10.1021/acs.orglett.2c00326 |
| Access Level: | acceso abierto |
| Palavra-chave: | 54 |
| Resumo: | We describe an asymmetric organocatalytic method to synthesize 1,7-dicarbonyl compounds containing a β-stereocenter. The chemistry relies on the formation of γ-keto radicals, generated upon oxidative ring-opening of cyclobutanols mastered by an organic photoredox catalyst. These non-stabilized primary radicals are stereoselectively intercepted by an iminium ion intermediate, formed upon activation of aliphatic and aromatic enals by a chiral secondary amine catalyst. This organocatalytic photoredox method served to prepare scaffolds found in natural products and drug molecules. |
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