Lega, Matteo
(2014)
DEVELOPMENT OF CHIRAL LIGANDS FROM NATURAL MOLECULES FOR METAL-PROMOTED ASYMMETRIC CATALYSIS.
[Tesi di dottorato]
Tipologia del documento: |
Tesi di dottorato
|
Lingua: |
English |
Titolo: |
DEVELOPMENT OF CHIRAL LIGANDS FROM NATURAL MOLECULES FOR METAL-PROMOTED ASYMMETRIC CATALYSIS |
Autori: |
Autore | Email |
---|
Lega, Matteo | matteoleg@libero.it |
|
Data: |
14 Marzo 2014 |
Numero di pagine: |
139 |
Istituzione: |
Università degli Studi di Napoli Federico II |
Dipartimento: |
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 | [non definito] |
|
Data: |
14 Marzo 2014 |
Numero di pagine: |
139 |
Parole chiave: |
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 |
[error in script]
[error in script]
Depositato il: |
10 Apr 2014 08:04 |
Ultima modifica: |
27 Gen 2015 15:41 |
URI: |
http://www.fedoa.unina.it/id/eprint/9636 |
Abstract
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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