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EnglishIn this paper, we report for the first time a stereoselective synthesis of biologically remarkable hydantoins through an intramolecular anti-aza-Michael addition, activated by the Trametes versicolor Laccase enzyme. This simple and straightforward synthesis affords the products with good yields. A study of the reaction mechanism has been carried out based on DFT calculations, showing that the only possible pathway at room temperature is the anti-aza-Michael addition, due to the very low free energy of activation barrier. We also show that the selective formation of the more stable Z-diastereomer is due to the greater stability of the appropriate conformer during the re-aromatization of the system.
| Titolo: | Bio-activated intramolecular: Anti -aza-Michael addition: Stereoselective synthesis of hydantoin derivatives |
| Autori interni: | TRINGALI, Corrado (Ultimo) (Corresponding) |
| Data di pubblicazione: | 2018 |
| Rivista: | |
| Handle: | http://hdl.handle.net/20.500.11769/361414 |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
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http://hdl.handle.net/20.500.11769/361414
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