Borrego, Lorenzo GRecio, RocíoMoreno, NazaretChelouan, AhmedÁlvarez, EleuterioSánchez-Coronilla, AntonioCaro, CarlosPearson, John RGarcía-Martín, Maria LuisaKhiar, NoureddineFernández, Inmaculada2023-05-032023-05-032022-09-01http://hdl.handle.net/10668/22187The stereoselective addition of ethyl acetate enolate to the C═N bond of N-tert-butylsulfinylimines has been investigated in depth. A significant effect of the LHMDS amount and the N-sulfinylimine nature on the stereoselectivity of the process was observed. Conditions were found where sulfinylimines of differently substituted salicylaldehydes derivatives, ethyl acetate, and LHMDS afforded the corresponding addition products as a single diastereomer in good yields. The developed protocol was successfully applied to the first stereoselective synthesis of differently substituted 4-amino-3,4-dihydrocoumarin derivatives. Computational models confirmed the prominent role of the ortho aryl substituent in the stereoselectivity of the process. A significant and selective cytotoxic activity against Glioblastoma Multiforme (GBM) cancer line has been determined for the noncyclic hydroxy ester derivative.enAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/Enantiopure 4-amino-3,4-dihydrocoumarinsGlioblastoma multiformeN-sulfinylaryliminesβ-hydroxyestersHumansGlioblastomaStereoisomerismEstersAntineoplastic Agentsresearch article36088758open access10.1016/j.ejmech.2022.1147301768-3254https://doi.org/10.1016/j.ejmech.2022.114730