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Estudio de la Reactividad del Benzoilnitrometano frente Aldehídos α,β Insaturados Alquílicos por Adición de Michael

dc.contributor.advisorVillamil, Mauricio Maldonado
dc.contributor.advisorGuevara Pulido, James Oswaldo
dc.creatorDavid Rodriguez, Fredy Alexander
dc.date.accessioned2020-08-07T02:22:13Z
dc.date.available2020-08-07T02:22:13Z
dc.date.created2020-05-18
dc.identifier.urihttps://repositorio.unal.edu.co/handle/unal/77976
dc.descriptionLa versión organocatalítica de la adición de Michael sigue atrayendo mucho interés, abarcando una amplia gama de aplicaciones sintéticas desde la formación de enlaces C-C y C- heteroátomo, además por su versatilidad en reacciones multicomponentes. Se han empleado a partir de las adiciones de Michael diferentes metilenos activados para la funcionalización β de aldehídos α, β insaturados, dada la versatilidad que ofrecen los productos de reacción como precursores o “building block” en síntesis química para estructuras más complejas. Los metilenos activados requieren un pro-nucleófilo que incorpore un hidrógeno C-H bastante ácido, por lo tanto, estudios recientes han señalado la existencia de una barrera de pKa para la activación de los nucleófilos que proceden por activación ion iminio. Los estudios han permitido observar unas características en el proceso y los productos obtenidos relacionado con el tipo de nucleófilo empleado y en particular con su valor de pKa en los hidrógenos del carbono α. Por lo tanto, en el presente trabajo se evaluó la reactividad del benzoilnitrometano frente a tres enales alquílicos que son crotonal, trans-2-pentenal y trans-2-hexenal, lo que permitió la caracterización de los compuestos 3- (2-fenil-1-nitro-2-oxoetil) hexanal (1a), 2-etoxi-6-fenil-5-nitro-4-propil-3,4-dihidro-2H-pirano (2a) y 5-benzoil-4,6-dimetil-5-nitrociclohex-1-enecarbaldehído (2b). Además, se pudo describir los diferentes mecanismos por los cuales se obtuvieron los productos, que involucraron reacciones domino. Otro hecho importante es la obtención de bueno y excelente excesos enantioméricos para los productos 2a y 2b. Se observó que la reactividad depende del sustituyente del aceptor, y además se demuestra la efectividad en la utilización de cetona con valor de pKa fuera de los limites descritos.
dc.description.abstractThe organocatalytic version of Michael's addition continues to attract much interest, encompassing a wide range of synthetic applications from the formation of C-C and C-heteroatom bonds, in addition to its versatility in multicomponent reactions. Different activated methylenes have been used from the Michael additions for β functionalization of α, β unsaturated aldehydes, given the versatility offered by reaction products as precursors or "building blocks" in chemical synthesis for more complex structures. Activated methylenes require a pro-nucleophile that incorporates a fairly acidic C-H hydrogen, therefore, recent studies have indicated the existence of a pKa barrier for the activation of nucleophiles that proceed by iminium ion activation. The studies have allowed us to observe some characteristics in the process and the products obtained related to the type of nucleophile used and in particular with its pKa value in the α carbon hydrogens. Therefore, in this work we evaluated the reactivity of benzoylnitromethane against three alkyl enals that are crotonal, trans-2-pentenal and trans-2-hexenal, which allowed the characterization of compounds 3- (2-phenyl-) 1-nitro-2-oxoethyl) hexanal (1a), 2-ethoxy-6-phenyl-5-nitro-4-propyl-3,4-dihydro-2H-pyran (2a) and 5-benzoyl-4,6- dimethyl-5-nitrocyclohex-1-enecarbaldehyde (2b). In addition, it was possible to describe the different mechanisms by which the products were obtained, which involved domino reactions. Another important fact is the obtaining of good and excellent enantiomeric excesses for products 2a and 2b. It was observed that the reactivity depends on the substituent of the acceptor, and also the effectiveness in the use of ketone with pKa value outside the limits described is demonstrated.
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dc.language.isospa
dc.rights.urihttp://creativecommons.org/licenses/by-nd/2.5/co/
dc.subjectacidez
dc.subjectorganocatálisis asimétrica
dc.subjectreacciones domino
dc.subjectadición de michael
dc.subject.ddc547 - Química orgánica
dc.titleEstudio de la Reactividad del Benzoilnitrometano frente Aldehídos α,β Insaturados Alquílicos por Adición de Michael
dc.typeOther
dc.rights.spaAcceso abierto
dc.contributor.institutionUniversidad Nacional de Colombia - Sede Bogotá
dc.subject.keywordacidity
dc.subject.keywordasymmetric organocatalysis
dc.subject.keyworddomino reactions
dc.subject.keywordaddition michael
dc.type.spaOtro
dc.type.hasversionPublished Version
dc.coverage.programDepartamento de Química
dc.contributor.gruplacAplicaciones Analíticas de Compuestos Orgánicos (AACO)
dc.description.additionalLínea de Investigación: Síntesis Orgánica
dc.coverage.modalityMaestria
dc.rights.accessRightsOpen Access
dc.rights.ccAtribución-SinDerivadas 2.5 Colombia
dc.rights.ccAtribución-SinDerivadas 2.5 Colombia
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