This doctoral thesis focuses on applying different organocatalysts in several enantioselective reactions and aerobic photooxidations using visible light. Chapter 1 describes using a chiral primary amine-salicylamide derived from (1R,2R)-cyclohexane-1,2-diamine as chiral organocatalyst in the asymmetric conjugate Michael addition of aldehydes and ketones to maleimides, giving the corresponding enantioenriched succinimides. The same organocatalyst is used in the enantioselective Michael addition of aldehydes to nitroalkenes, yielding enantiopure γ-nitroaldehydes. Furthermore, these Michael additions of aldehydes to maleimides and nitroalkenes are carried out employing sustainable and environmentally friendly deep eutectic solvents (DES), being able to reuse the catalytic system for several cycles. Chapter 2 describes using a chiral primary-amine monocarbamate derived from (1R,2R)-cyclohexane-1,2-diamine as chiral organocatalyst in the enantioselective α-amination of aldehydes with azodicarboxylates, obtaining the corresponding α,α-disubstituted aldehydes with the absence of solvent under mild conditions. This simple orgacatalytic system’s applicability is demonstrated by preparing a chiral oxazolidinone precursor of amino acids. The reaction is also successfully scaled-up. In addition, theoretical calculations were performed to demonstrate how the absolute configuration of the final adducts is produced. Chapter 3 shows how riboflavin tetraacetate, a cheap vitamin B2 derivative, is an appropriate metal-free photocatalyst in the aerobic photooxidation of xanthenes, thioxanthenes and dihydroacridines under visible light irradiation. / This research work has been possible thanks to funding from the Spanish Ministerio de Economía y Competitividad (PGC2018-096616-B-100, CTQ201788171-P), the Generalitat Valenciana (AICO 2021/013) and the University of Alicante (VIGROB-173). The author wishes to express his gratitude to the Institute of Organic Synthesis for a research contract (I-PI/21-20) and to the University of Alicante-Banco Santander consortium for a grant to spend a three-months research period in the Chemistry Interdisciplinary Project research center (ChIP) of the University of Camerino (Italy) under the supervision of Dr. Matteo Tiecco.
| Identifer | oai:union.ndltd.org:ua.es/oai:rua.ua.es:10045/136244 |
| Date | 26 May 2023 |
| Creators | Torregrosa-Chinillach, Alejandro |
| Contributors | Chinchilla, Rafael, Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
| Publisher | Universidad de Alicante |
| Source Sets | Universidad de Alicante |
| Language | English |
| Detected Language | English |
| Type | info:eu-repo/semantics/doctoralThesis |
| Rights | Licencia Creative Commons Reconocimiento-NoComercial-SinObraDerivada 4.0, info:eu-repo/semantics/openAccess |
| Relation | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PGC2018-096616-B-I00, info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-88171-P |
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