Diastereodivergent organocatalysis for the asymmetric synthesis of chiral annulated furans
<p> Disclosed herein is a stereoselective method for the synthesis of 2,3-furan fused carbocycles bearing adjacent quaternary and tertiary carbon stereocenters. The chemistry is based on an asymmetric addition of b-ketoesters to 2-(1-alkynyl)-2-alkene-1-ones catalysed by natural cinchona alkal...
| 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:2072/305774 |
| Acceso en línea: | http://hdl.handle.net/2072/305774 https://doi.org/10.1039/c5sc01052g |
| Access Level: | acceso abierto |
| Sumario: | <p> Disclosed herein is a stereoselective method for the synthesis of 2,3-furan fused carbocycles bearing adjacent quaternary and tertiary carbon stereocenters. The chemistry is based on an asymmetric addition of b-ketoesters to 2-(1-alkynyl)-2-alkene-1-ones catalysed by natural cinchona alkaloids followed by a silver-catalysed intramolecular cycloisomerisation. By exploiting the distinct catalysis modes of quinine, which can act either as a general base or, upon opportune modifications, as a phase transfer catalyst, a complete switch of the enforced sense of diastereoinduction is achieved. The stereodivergent systems enable access to the full matrix of all possible stereoisomeric products.</p> <p> </p> |
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