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Issue 22, 2018
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Bio-activated intramolecular anti-aza-Michael addition: stereoselective synthesis of hydantoin derivatives

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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.

Graphical abstract: Bio-activated intramolecular anti-aza-Michael addition: stereoselective synthesis of hydantoin derivatives

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Publication details

The article was received on 11 Jun 2018, accepted on 29 Sep 2018 and first published on 01 Oct 2018


Article type: Paper
DOI: 10.1039/C8NJ02909A
Citation: New J. Chem., 2018,42, 18348-18357

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    Bio-activated intramolecular anti-aza-Michael addition: stereoselective synthesis of hydantoin derivatives

    V. M. Bhusainahalli, A. Rescifina, N. Cardullo, C. Spatafora and C. Tringali, New J. Chem., 2018, 42, 18348
    DOI: 10.1039/C8NJ02909A

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