Enantiodivergent Synthesis of (+)- and (-)-Pyrrolidine 197B. Synthesis of trans-2,5-Disubstituted Pyrrolidines via Intramolecular Hydroamination
A highly efficient diastereoselective iron(III)-catalyzed intramolecular hydroamination/cyclization reaction involving - substituted amino alkenes is described. Thus, enantiopure trans-2,5- disubstituted pyrrolidines and trans-5-substituted proline derivatives are synthesized by means of the combin...
| Autores: | , , , , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2016 |
| País: | España |
| Institución: | Universidad de La Laguna (ULL) |
| Repositorio: | RIULL. Repositorio Institucional de la Universidad de La Laguna |
| OAI Identifier: | oai:riull.ull.es:915/16011 |
| Acceso en línea: | http://riull.ull.es/xmlui/handle/915/16011 |
| Access Level: | acceso abierto |
| Palabra clave: | Alcaloides ciclización hidroaminación acero heterociclos de nitrógeno |
| Sumario: | A highly efficient diastereoselective iron(III)-catalyzed intramolecular hydroamination/cyclization reaction involving - substituted amino alkenes is described. Thus, enantiopure trans-2,5- disubstituted pyrrolidines and trans-5-substituted proline derivatives are synthesized by means of the combination of enantiopure starting materials, easily available from L--amino acids, with sustainable metal catalysts such as iron(III) salts. The scope of this methodology is highlighted in an enantiodivergent approach to the synthesis of both (+)- and (-)-pyrrolidine 197B alkaloids from L-glutamic acid. In addition, a computational study was also carried out to gain insight into the complete diastereoselectivity of the transformation. |
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