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Amino Alcohols and Diamines: Novel Syntheses of Enantiopure Molecules useful in Catalysis

By Davide Fratoni

Abstract

The subject of this PhD thesis is in the synthesis of new chiral amino alcohols and diamines using several\ud strategies. In the first part has been reported the syntheses, the attribution of absolute configuration and\ud the spectroscopic characterization of new chiral diamines, amino alcohols and polyfunctionalized ligands based on monoterpenes backbone, in particular (-)-limonene and (+)-3-carene. In the second part of this thesis were reported new synthetic strategies to obtain several functionality through Betti type reactions, using different starting materials and reaction’s conditions. Thank to these new synthetic variants it was possible to obtain chiral arylglycinates, a class of unnatural amino acids, aminocicloalyl naphthols and phenols, used as chiral ligands in asymmetric synthesis, chiral bifunctionalized (thio)ureas, largely applied as organocatalysts, benzochromenes, a class of biologically active compounds with a wide spectrum of activities and widely employed as cosmetics, pigments and potential biodegradable agrochemicals, and diamino alkyl naphthols, potentially useful as catalyst in asymmetric synthesis. Moreover, have been applied some Betti’s bases as catalysts in the enantioselective addition of diethyl zinc on α,β-unsaturated\ud carbonyl compounds and in the reduction of prochiral ketones with borane, both with good yields but with\ud moderate enantiomeric excesses. Finally, in the last part of this thesis has been proposed a new synthetic route to obtain 4-fluorothreonine, a fluorinated natural amino acid, through a greener and simpler way than that known in the literature

Topics: CHIM/06 Chimica organica
Year: 2012
OAI identifier: oai:ecum.eprints.org:320
Provided by: CamEPrints
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