Assessing the versatility of organocatalysis as a strategy for enabling novel asymmetric transformations
In a first project, we developed the direct asymmetric -alkylation of -branched enals exploiting the compatibility between dienamine activation and Brønsted acid catalysis. In a subsequent study, the mild conditions provided by organocatalysis allowed for the use of dioxindole and its analogues to...
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| Tipo de recurso: | tesis doctoral |
| Estado: | Versión publicada |
| Fecha de publicación: | 2013 |
| País: | España |
| Institución: | Universitat Rovira i virgili (URV) |
| Repositorio: | Repositori Institucional de la Universitat Rovira i Virgili |
| OAI Identifier: | oai:urv.cat:TDX:1432 |
| Acceso en línea: | https://hdl.handle.net/20.500.11797/TDX1432 http://hdl.handle.net/10803/284153 |
| Access Level: | acceso abierto |
| Palabra clave: | 547 - Química orgànica 542 - Química pràctica de laboratori. Química preparativa i experimental 54 - Química |
| Sumario: | In a first project, we developed the direct asymmetric -alkylation of -branched enals exploiting the compatibility between dienamine activation and Brønsted acid catalysis. In a subsequent study, the mild conditions provided by organocatalysis allowed for the use of dioxindole and its analogues to access valuable enantioenriched chiral 3-hydroxyoxindoles. Moreover, the versatility of organocatalysis enabled the unprecedented employment of anion-binding catalysis to control the reactivity of a photoredox-generated ion-pair intermediate as a new methodology for the enantioselective oxidative Mannich-type functionalization of tetrahydroisoquinolines. Finally we found that the photochemical activity of electron donor-acceptor (EDA) complexes, generated between electron-poor benzylic substrates and perfluorohexyl iodide, enables the direct perfluoro-alkylation of arenes driven by visible light. |
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