Diastereodivergent Enantioselective [8+2] Annulation of Tro- pones and Enals Catalyzed by N-Heterocyclic Carbenes
N-Heterocyclic carbene (NHC) catalysts are used for the first time to mediate asymmetric [8+2] cycloadditions of enals with tropones. The kinetic [8+2] cis-cycloadducts can be epimerized to their trans analogues by simply using increased amounts of base and longer reaction times. Substituted tropone...
| Autores: | , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2019 |
| 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:2072/374855 |
| Acceso en línea: | http://hdl.handle.net/2072/374855 https://doi.org/10.1021/acs.orglett.9b00906 |
| Access Level: | acceso abierto |
| Palabra clave: | 54 |
| Sumario: | N-Heterocyclic carbene (NHC) catalysts are used for the first time to mediate asymmetric [8+2] cycloadditions of enals with tropones. The kinetic [8+2] cis-cycloadducts can be epimerized to their trans analogues by simply using increased amounts of base and longer reaction times. Substituted tropones are also tolerated, and the cycloaddition products can be derivatized by hydrogenation or methanolysis. The main stereochemical features on the results of DFT calculations. |
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