In 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.
Bio-activated intramolecular: Anti -aza-Michael addition: Stereoselective synthesis of hydantoin derivatives
Bhusainahalli, Vedamurthy M.Primo
;Rescifina, Antonio
;Cardullo, Nunzio;Spatafora, Carmela;Tringali, Corrado
Ultimo
2018-01-01
Abstract
In 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.File | Dimensione | Formato | |
---|---|---|---|
Bio-activated intramolecular anti-aza-Michael addition.pdf
solo gestori archivio
Tipologia:
Versione Editoriale (PDF)
Licenza:
NON PUBBLICO - Accesso privato/ristretto
Dimensione
1.87 MB
Formato
Adobe PDF
|
1.87 MB | Adobe PDF | Visualizza/Apri |
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.