Enantiodivergent Synthesis of (+)- and (-)-Pyrrolidine 197B. Synthesis of trans-2,5-Disubstituted Pyrrolidines via Intramolecular Hydroamination
| Autor: | Pérez, Sixto J., Purino, Martín A., Cruz, Daniel A., López-Soria, Juan M., Carballo, Rubén M., Ramírez, Miguel A., Fernández, Israel, Martín García, Víctor Sotero, Padrón, Juan I. |
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| Rok vydání: | 2016 |
| Předmět: | |
| Zdroj: | RIULL. Repositorio Institucional de la Universidad de La Laguna Universidad de La Laguna (ULL) |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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