Lega, Matteo (2014) DEVELOPMENT OF CHIRAL LIGANDS FROM NATURAL MOLECULES FOR METAL-PROMOTED ASYMMETRIC CATALYSIS. [Tesi di dottorato]
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| Item Type: | Tesi di dottorato |
|---|---|
| Resource language: | English |
| Title: | DEVELOPMENT OF CHIRAL LIGANDS FROM NATURAL MOLECULES FOR METAL-PROMOTED ASYMMETRIC CATALYSIS |
| Creators: | Creators Email Lega, Matteo matteoleg@libero.it |
| Date: | 14 March 2014 |
| Number of Pages: | 139 |
| Institution: | Università degli Studi di Napoli Federico II |
| Department: | Scienze Chimiche |
| Scuola di dottorato: | Scienze chimiche |
| Dottorato: | Scienze chimiche |
| Ciclo di dottorato: | 26 |
| Coordinatore del Corso di dottorato: | nome email Paduano, Luigi luigi.paduano@unina.it |
| Tutor: | nome email Ruffo, Francesco UNSPECIFIED |
| Date: | 14 March 2014 |
| Number of Pages: | 139 |
| Keywords: | Asymmetric Catalysis, carbohydrates ligands, green chemistry |
| Settori scientifico-disciplinari del MIUR: | Area 03 - Scienze chimiche > CHIM/03 - Chimica generale e inorganica |
| Aree tematiche (7° programma Quadro): | AMBIENTE (INCLUSO CAMBIAMENTO CLIMATICO) > Migliorare l'efficienza delle risorse |
| Date Deposited: | 10 Apr 2014 08:04 |
| Last Modified: | 27 Jan 2015 15:41 |
| URI: | http://www.fedoa.unina.it/id/eprint/9636 |
Collection description
The main aim of this PhD thesis was the development of a new family of chiral ligands derived from D-glucose (elpaN-type). These ligands were designed in order to be pseudo-enantiomeric respect to the previously developed Naple-type family, and focusing on the obtainment of easy and straightforward synthesis. On this basis, three libraries of elapN-type ligands were prepared and successfully employed in homogenous metal-promoted asymmetric catalysis: the elpaN-phos, for the Pd-promoted Asymmetric Allylic Substitution; the elpaN-py, for the Mo-promoted Asymmetric Allylic Alkylation enhanced by microwaves; the elpaN-Salen, for the Mn-promoted Asymmetric Epoxidation. In all cases, performances were excellent and inversion of selectivity respect to the Naple-type family was achieved. In the particular case of the elpaN-phos subset, a phase-tagged version of the ligand was successfully employed in multiphase catalysis, achieving the recycle of the catalyst. The secondary aim of this PhD thesis was the development of a library of sugar-derived, water soluble Pd0 complexes for aqueous Suzuki-Miyaura cross-coupling. Also in this case, good performances were obtained (TOF up to 9500 h-1), among the best in literature for this reaction in aqueous, sustainable condition.
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