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

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.
Catalysis; Chemistry (all); Materials Chemistry2506 Metals and Alloys
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/20.500.11769/361414
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