Synthesis of enantiopure analogues of 3-hydroxyproline and derivatives
All four enantiomerically pure 2-hydroxy-7-azabicyclo[2.2.1]heptane-1-carboxylic acids, novel restricted analogues of 3-hydroxyproline, are described. The synthesis starts with the Diels-Alder reaction between methyl 2-benzamidoacrylate and Danishefsky's diene and uses as key steps a base-promo...
| Autores: | , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2002 |
| País: | España |
| Institución: | Universidad de La Rioja (UR) |
| Repositorio: | RIUR. Repositorio Institucional de la Universidad de La Rioja |
| OAI Identifier: | oai:portal.dialnet.es:doc/5bbc6908b750603269e813dc |
| Acceso en línea: | https://investigacion.unirioja.es/documentos/5bbc6908b750603269e813dc |
| Access Level: | acceso abierto |
| Sumario: | All four enantiomerically pure 2-hydroxy-7-azabicyclo[2.2.1]heptane-1-carboxylic acids, novel restricted analogues of 3-hydroxyproline, are described. The synthesis starts with the Diels-Alder reaction between methyl 2-benzamidoacrylate and Danishefsky's diene and uses as key steps a base-promoted internal nucleophilic displacement of the methanesulfonate group in the cyclohexane ring, followed by a resolution method that involves formation of diastereomers and further separation by crystallization. This synthetic route allowed us to obtain both enantiomers of the N-Boc-7-azabicyclo[2.2.1]heptan-2-ones, valuable ketones used as precursors of (-)- and (+)-epibatidine and other more interesting analogues. © 2002 Published by Elsevier Science Ltd. |
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