Enantioselective α-Amination of 1,3-Dicarbonyl Compounds in Batch and Flow with Immobilized Thiourea Organocatalysts
<p> A polymer-supported bifunctional thiourea organocatalyst (<strong>PS</strong>-<strong>TU</strong>) has been prepared and successfully used in the enantioselective a-amination of 1,3-dicarbonyl compounds with azodicarboxylates. In contrast with homogeneous thioureas,...
| Autores: | , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2015 |
| 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:2072/305816 |
| Acceso en línea: | http://hdl.handle.net/2072/305816 https://doi.org/10.1039/c5gc00496a |
| Access Level: | acceso abierto |
| Sumario: | <p> A polymer-supported bifunctional thiourea organocatalyst (<strong>PS</strong>-<strong>TU</strong>) has been prepared and successfully used in the enantioselective a-amination of 1,3-dicarbonyl compounds with azodicarboxylates. In contrast with homogeneous thioureas, <strong>PS</strong>-<strong>TU</strong> is not irreversibly deactivated by the azodicarboxylate reagents, and simple washing with triethylamine between runs has allowed the repeated reuse (9 cycles) of the <strong>PS</strong>-<strong>TU</strong> catalyst. The a-amination mediated by <strong>PS</strong>-<strong>TU</strong> has also been adapted to perform the enantioselective amination (93% ee) of ethyl 2-oxocyclopentanecarboxylate in continuous flow (7.5 h operation, 21 min residence time, TON = 37).</p> |
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