Jump to main content
Jump to site search


Bio-Activated Intramolecular Anti-Aza-Michael Addition: Stereoselective Synthesis of Hydantoin Derivatives

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 an anti-aza-Michael addition, due to the very low free energy of activation barrier. We also show as 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.

Back to tab navigation

Supplementary files

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, Accepted Manuscript
  •   Request permissions

    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, Accepted Manuscript , DOI: 10.1039/C8NJ02909A

Search articles by author

Spotlight

Advertisements