Lega, Matteo (2014) DEVELOPMENT OF CHIRAL LIGANDS FROM NATURAL MOLECULES FOR METAL-PROMOTED ASYMMETRIC CATALYSIS. [Tesi di dottorato]

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Tipologia del documento: Tesi di dottorato
Lingua: English
Titolo: DEVELOPMENT OF CHIRAL LIGANDS FROM NATURAL MOLECULES FOR METAL-PROMOTED ASYMMETRIC CATALYSIS
Autori:
AutoreEmail
Lega, Matteomatteoleg@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:
nomeemail
Paduano, Luigiluigi.paduano@unina.it
Tutor:
nomeemail
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
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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