Development of Innovative Organocatalytic Methodologies and Synthesis of New QCA Candidates through Reactions with Carbocations

Mengozzi, Luca (2016) Development of Innovative Organocatalytic Methodologies and Synthesis of New QCA Candidates through Reactions with Carbocations, [Dissertation thesis], Alma Mater Studiorum Università di Bologna. Dottorato di ricerca in Chimica, 28 Ciclo. DOI 10.6092/unibo/amsdottorato/7446.
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During the PhD Luca Mengozzi studied reactions involving carbocations or carbocationic intermediates to develop new synthetic methodologies, and a new generation of quantum cellular automata (QCA) candidates in the context of the European Project Molarnet. Concerning the development of new asymmetric methodologies, he studied in detail the stereoselective alkylation of aldehydes with isoquinolinium and quinolinium ions generated in situ. These reactions were promoted by chiral secondary amine catalysts and no metals are needed. The first alkylation of acyl isoquinolinium ions with aldehydes was reported and it was applied to the first enantioselective synthesis of 13-alkyl tetrahydroprotoberberine alkaloids. Preliminary tests on resistant tumor cell lines performed by prof. Calonghi revealed promising cytotoxic activities. An asymmetric Pictet Spengler reaction to access 1-allyl isoquinolines was also reported. He studied the activation of carboxylic acids and their alkylation with stable carbenium ions promoted by chiral isothioureas and the development of the first photocatalytic alkylation of aldehydes promoted by iron photosensitizers. He spent five months as a visiting PhD student in Prof. Pericás Research group at ICIQ, Tarragona, Spain. During this period he studied the use of flow chemistry techniques for the synthesis of antiviral agent (-)-oseltamivir. In particular he studied the use of supported organocatalsyts in the enantiodetermining step of the synthetic pathway. QCA are a new paradigm for molecular computation and he worked on the synthesis of new candidates applying the knowledge of the research group on SN1 reactions. Through this strategy a new class of ferrocene guanines conjugates, ferrocene porphyrins, and ferrocene containing aluminium salophen complexes were obtained. The study of their properties on different surfaces that revealed the formation of interesting self-assembled monolayers for both salophen complexes and porphyrins. One paper was published and three are in preparation with our Molarnet partners.

Tipologia del documento
Tesi di dottorato
Mengozzi, Luca
Dottorato di ricerca
Scuola di dottorato
Scienze chimiche
Settore disciplinare
Settore concorsuale
Parole chiave
carbocations – organocatalysis – QCA – molecular computation - enantioselective alkylations – isoquinoline –alkaloids – enamine catalysis - quinoline – isothioureas –photocatalysis – [Fe(bpy)3]Br2 – radicals - oseltamivir – flow chemistry
Data di discussione
18 Aprile 2016

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