Regio- e stereocontrollo nell'addizione viniloga di alchilidenossindoli a nitrostireni via organocatalisi.

di Iorio, Nicola (2013) Regio- e stereocontrollo nell'addizione viniloga di alchilidenossindoli a nitrostireni via organocatalisi. [Laurea magistrale], Università di Bologna, Corso di Studio in Chimica industriale [LM-DM270]
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Abstract

The topic of this work is the simultaneous activation, promoted by 9-epi-NH2-DHQA-TU, of alkylideneoxindole and nistirene derivatives, respectively via base catalysis and hydrogen-bond catalysis. The chosen substrates, of high biological interest, are used as starting materials for a vinylogous Michael addition where we wish to control the stereochemistry of the two asymmetric carbons far away from the active site, respectively in γ and δ position. Due to the particular structure of the starting oxindoles, it is hereby presented the first variant of this reaction performed at its highest level of stereochemical complexity. It is possible as a matter of fact, to generate 24 isomers of the product. Specifically, given that the nucleophilic attack can occur from various, non equivalent regions of the starting molecule, our main goal was to achieve a complete regio- and stereocontrol of the reaction. We have verified that the reported organocatalyzed vinylogous reaction represents a valid integration of the metal-catalyzed one, since it affords highly stereochemically complex products in good to high yields and excellent optical purity.

Abstract
Tipologia del documento
Tesi di laurea (Laurea magistrale)
Autore della tesi
di Iorio, Nicola
Relatore della tesi
Scuola
Corso di studio
Ordinamento Cds
DM270
Parole chiave
base catalysis oxindole nitrostyrene Michael addition vinylogous
Data di discussione della Tesi
18 Ottobre 2013
URI

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