Fernández Fernández, InmaculadaRecio Jiménez, RocíoMartínez Carrasquilla, Laura2016-11-242016-11-242016Martínez Carrasquilla, L. (2016). Síntesis estereoselectiva de nuevos inhibidores de la agregación plaquetaria. (Trabajo fin de grado inédito). Universidad de Sevilla, Sevilla.http://hdl.handle.net/11441/49109Chirality is a feature instrinsically linked to life. For this reason, the use of stereochemically pure compounds presents numerous advantages compared to the use of racemates in pharmaceutical industry. Therefore, the present work is a part of a broader project aimed to the development of new strategies for the design and the stereoselective synthesis of chiral compounds with biological activity. In particular, we focus on the enantioselective synthesis of a new family of 4-aminocroman-2-one derivatives as antiplatelet drugs and their phosphorated analogous. These compounds constitute the basic structure of a family of inhibitors of platelet aggregation, modulator of thrombus formation, whose synthesis in optically pure form has not been developed so far. Our methodology is based on the efficiency of the tert-butylsulfinylsulfinil group as chiral inductor in nucleophilic additions to chiral N-sulfinylimines. On the one hand, the addition of the ethyl acetate anion allows the preparation of the corresponding optically pure 2-aminocromanones. On the other hand, the addition of the methyl phenylphosphinate carbanion leads to the corresponding phosphinyl bioisosteres. In both cases, the addition takes place stereoselectively and it allows, for the first time, the preparation of a diverse array of enantiopure 4-amino-croman-2-one derivatives, allowing the study of the activity of both enantiomers separately. To sum up, we have developed a new, general, easy, effective and modular methodology for the stereoselective synthesis of both enantiomers of a wide range o β-amino esters, which constitute a new family of pharmacologically relevant compoundsapplication/pdfspaAttribution-NonCommercial-NoDerivatives 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc-nd/4.0/Asymmetric synthesisAntiplatelet drugsN-sulfinyliminesEnantiopure 4-aminocroman-2-oneinfo:eu-repo/semantics/bachelorThesisinfo:eu-repo/semantics/openAccess