Synthesis of diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6-dicarboxylate by Pd-catalyzed intramolecular allylic alkylation. Stereoselective preparation of its optically homogeneous form from R-(−)-carvone
[EN]A new route to racemic diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6- dicarboxylate (±)-1a by means of a palladium-catalyzed intramolecular allylic alkylation exercised on malonate-ester derivatives has been developed from R-(-)-carvone. The stereocontrolled synthesis of the enantiomerically pur...
| Autores: | , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión borrador |
| Fecha de publicación: | 2010 |
| País: | España |
| Institución: | Universidad de Salamanca (USAL) |
| Repositorio: | GREDOS. Repositorio Institucional de la Universidad de Salamanca |
| OAI Identifier: | oai:gredos.usal.es:10366/170166 |
| Acceso en línea: | http://hdl.handle.net/10366/170166 |
| Access Level: | acceso abierto |
| Palabra clave: | Allylic alkylation Monoterpenes Pd catalysis Stereoselective synthesis |
| Sumario: | [EN]A new route to racemic diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6- dicarboxylate (±)-1a by means of a palladium-catalyzed intramolecular allylic alkylation exercised on malonate-ester derivatives has been developed from R-(-)-carvone. The stereocontrolled synthesis of the enantiomerically pure (-)-1b by application of a six-step reactions sequence with a 28% overall yield from acetal 8, has been accomplished. |
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