New methodologies in organocatalysis: from discovery to application and mechanistic

Bisag, Giorgiana Denisa (2023) New methodologies in organocatalysis: from discovery to application and mechanistic, [Dissertation thesis], Alma Mater Studiorum Università di Bologna. Dottorato di ricerca in Chimica, 35 Ciclo. DOI 10.48676/unibo/amsdottorato/10627.
Documenti full-text disponibili:
[img] Documento PDF (English) - Richiede un lettore di PDF come Xpdf o Adobe Acrobat Reader
Disponibile con Licenza: Creative Commons Attribution Non-commercial No Derivatives 4.0 (CC BY-NC-ND 4.0) .
Download (9MB)


This PhD thesis deals with three different topics: i) sulfoxonium ylides, ii) donor-acceptor cyclopropanes, and iii) desymmetrization reactions. Catalysis, and in more detail organocatalysis, is the fil rouge linking the three subjects of study. The main focus treated during this doctorate period is the reactivity of sulfoxonium ylides, and in particular stabilized sulfoxonium ylides. Special attention has been dedicated to the behavior of these particular substrates under asymmetric and non-asymmetric reaction conditions. Moreover, also similarities and differences with the related, less stable, sulfonium ylides were fully analyzed, both experimentally and from a theoretical point of view. Two different reactions were developed in full. One conducted under acidic reaction conditions and the second one exploiting the asymmetric aminocatalysis. Subsequently, the reactivity of donor-acceptor cyclopropanes was studied. After different attempts in the development of a new catalytic methodology based on these substrates, a non-conventional reactivity conducted under phase transfer catalysis was discovered and optimized. In particular, a chemodivergent reaction depending on the reaction conditions was developed. Finally, during the period spent abroad, a preliminary study of a desymmetrization reaction was carried out. The studied reaction is based on an asymmetric elimination reaction conducted under asymmetric phosphoric acid catalysis. In summary, this PhD thesis shows the versatility of different organocatalytic methodologies when applied to different reactions and substrates.

Tipologia del documento
Tesi di dottorato
Bisag, Giorgiana Denisa
Dottorato di ricerca
Settore disciplinare
Settore concorsuale
Parole chiave
organicatalisi, ilidi di solfossonio, chemodivergenza, desimmetrizazione
Data di discussione
23 Marzo 2023

Altri metadati

Statistica sui download

Gestione del documento: Visualizza la tesi