Data di Pubblicazione:
2017
Citazione:
STEREOSELECTIVE CATALYTIC REACTIONS UNDER CONTINUOUS FLOW CONDITIONS / R. Porta ; tutor: M. Benaglia; co-tutor: A. Puglisi. DIPARTIMENTO DI CHIMICA, 2017 Mar 28. 29. ciclo, Anno Accademico 2016. [10.13130/r-porta_phd2017-03-28].
Abstract:
This PhD Thesis deals with the application of different catalytic methodologies under continuous flow conditions. In particular, the combination of flow chemistry with different enabling technologies is explored.
In Chapter 1 the combination of continuous flow processes with the use of different solid supported chiral organocatalysts is described. The fabrication of chiral, packed-bed and monolithic, organocatalytic reactors and their use in stereoselective transformations are reported. The possibility to recycle the immobilized chiral catalysts is also discussed.
- In section 1.2 the use of polystyrene- and silica-supported chiral imidazolidinones to perform continuous flow stereoselective Diels-Alder cycloadditions and stereoselective aldehydes alkylation is studied.
- In section 1.3 the immobilization onto different materials of primary amines derived from Cinchona alkaloids and the application under flow conditions are explored.
- In section 1.4 chiral picolinamides for the continuous stereoselective reduction of imines with trichlorosilane are studied.
Chapter 2 describes the application of different synthetic strategies using flow micro(meso)-reactors, aimed to the synthesis of chiral active pharmaceutical ingredients or immediate advanced precursors of compounds of industrial interest. In particular,
- in section 2.2 the organocatalytic, stereoselective synthesis of (S)-Pregabalin and (S)-Warfarin within microreactors is investigated.
- Section 2.3 presents the continuous flow synthesis of primary amines through a metal-free reduction of nitro compounds with trichlorosilane.
- In section 2.4 a catalytic strategy for a multistep synthesis of chiral, biological active 1,2-amino alcohols using 3D-printed flow reactors is highlighted.
Chapter 3 covers the research work carried out during my research period in Aachen, Germany which was focused on the development of a new synthetic methodology using photoredox catalysis. In particular, the photocatalytic reductive coupling of imine with olefins for the preparation of -amino esters and its application under continuous flow conditions are discussed.
Tipologia IRIS:
Tesi di dottorato
Elenco autori:
R. Porta
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