Intramolecular hydrogen bond activation for kinetic resolution of furanone derivatives by an organocatalyzed [3+2] asymmetric cycloaddition
Herein, a formal highly enantioselective organocatalyzed [3+2] cycloaddition of furanone derivatives and azomethine ylides is presented. The success of this reaction resides in an intramolecular hydrogen bond activation through an o-hydroxy group at aromatic ring of the imine, allowing the formation...
| Autores: | , , , , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2023 |
| País: | España |
| Institución: | Universidad Autónoma de Madrid |
| Repositorio: | Biblos-e Archivo. Repositorio Institucional de la UAM |
| Idioma: | inglés |
| OAI Identifier: | oai:repositorio.uam.es:10486/708736 |
| Acceso en línea: | http://hdl.handle.net/10486/708736 https://dx.doi.org/10.1039/D3QO01471A |
| Access Level: | acceso abierto |
| Palabra clave: | Intramolecular Hydrogen Furanone Cycloaddition Física Química |
| Sumario: | Herein, a formal highly enantioselective organocatalyzed [3+2] cycloaddition of furanone derivatives and azomethine ylides is presented. The success of this reaction resides in an intramolecular hydrogen bond activation through an o-hydroxy group at aromatic ring of the imine, allowing the formation of highly multifunctional bicyclic adducts with five stereogenic centers in a stereocontrolled manner. Furthermore, the reaction is paired to a highly efficient kinetic resolution of butenolides, achieving selectivity factors above 200. Using this methodology, furan-2(5H)-ones as well as furo[3,4-c]pyrrolidinones were obtained with high enantioselectivities. Quantum chemistry calculations reveal the crucial role of hydrogen bond formed between the catalyst donor-units and the two reagents, which modify their arrangement and promote effective facial discrimination resulting in a highly selective kinetic resolution. In addition, further applicability of the kinetic resolution process is shown |
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