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Archivio digitale delle tesi discusse presso l’Università di Pisa

Tesi etd-11212023-120741


Tipo di tesi
Tesi di laurea magistrale
Autore
MACCABRUNI, FABIO
URN
etd-11212023-120741
Titolo
Renewable resources for phosphorus ligands: synthesis of isosorbide derived biaryl monophosphites
Dipartimento
CHIMICA E CHIMICA INDUSTRIALE
Corso di studi
CHIMICA
Relatori
relatore Prof.ssa Iuliano, Anna
Parole chiave
  • phosphorus ligands
  • tropos
  • isosorbide
  • renewable resources
  • monophosphite
  • atroposiomer
Data inizio appello
11/12/2023
Consultabilità
Non consultabile
Data di rilascio
11/12/2026
Riassunto
This thesis work explored the synthesis and the characterization of isosorbide derived biaryl monophosphite as well as their use as chiral metal ligands for asymmetric catalysis.
Firstly, the concept of double asymmetric induction and tropos activation is discussed by reporting various examples of atropoisomeric and tropos monophosphite ligands. In the second section, the synthesis of the flexible biaryl scaffolds as well as the optimization of the synthesis of biaryl derived monophosphate ligands is reported.
The structural characterization of the monophosphite ligands by means of 1D and 2D NMR spectroscopies and their stereochemical characterization by means of VT 31P-NMR, CD and temperature dependent-CD spectroscopies is also discussed.
Finally, because the monophosphite ligands were essayed as chiral ligands in Rh-catalyzed asymmetric addition of arylboronic acid to electronpoor alkenes and in Rh-catalyzed asymmetric hydrogenation of dimethylitaconate, in the last part of the thesis these results are discussed.
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