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.
STEREOSELECTIVE CATALYTIC REACTIONS UNDER CONTINUOUS FLOW CONDITIONS / R. Porta ; tutor: M. Benaglia; co-tutor: A. Puglisi. - Milano : Università degli studi di Milano. DIPARTIMENTO DI CHIMICA, 2017 Mar 28. ((29. ciclo, Anno Accademico 2016.
|Titolo:||STEREOSELECTIVE CATALYTIC REACTIONS UNDER CONTINUOUS FLOW CONDITIONS|
|Data di pubblicazione:||28-mar-2017|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
Settore CHIM/04 - Chimica Industriale
|Citazione:||STEREOSELECTIVE CATALYTIC REACTIONS UNDER CONTINUOUS FLOW CONDITIONS / R. Porta ; tutor: M. Benaglia; co-tutor: A. Puglisi. - Milano : Università degli studi di Milano. DIPARTIMENTO DI CHIMICA, 2017 Mar 28. ((29. ciclo, Anno Accademico 2016.|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.13130/r-porta_phd2017-03-28|
|Appare nelle tipologie:||Tesi di dottorato|