Multicomponent approach to silica-grafted peptide catalysts : A 3 D continuous-flow organocatalytic system with on-line monitoring of conversion and stereo-selectivity
Autor(a) principal: | |
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Data de Publicação: | 2014 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFSCAR |
Texto Completo: | https://repositorio.ufscar.br/handle/ufscar/8017 |
Resumo: | The derivatization of organocatalysts with functional appendages suitable to anchor onto solid supports is usually achieved by stepwise syntheses. As an alternative to such a strategy, this work describes a one-pot approach to silylated prolyl-peptide catalysts by a multicomponent reaction that enables the simultaneous incorporation of the catalytic and the heterogenizable (triethoxysilane) moieties. A microreactor with high catalytic efficacy and reproducibly in the conjugate addition of aldehydes to nitroolefins was obtained by grafting onto HPLC-grade silica (10 μm) and packing into a column with a selected catalyst. A 3 D continuous-flow system that includes the on-line monitoring of the reaction outcome was set up. For that, the microreactor was coupled to a chromatographic column for the separation of the remaining substrates from the Michael adduct in the second dimension, followed by a chiral polysaccharide column for the analysis of conversion and stereoselectivity. This approach represents a new instrumental setup that combines the advantages of multidimensional chromatography and flow catalysis. |
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Scatena, Gabriel dos SantosPaixão, Márcio Weberhttp://lattes.cnpq.br/3773908504964104Cass, Quezia Bezerrahttp://lattes.cnpq.br/9197210255594409http://lattes.cnpq.br/81229847403929154b49e73d-1509-4df2-b64a-be279d36ef4d2016-10-20T18:49:47Z2016-10-20T18:49:47Z2014-11-28SCATENA, Gabriel dos Santos. Multicomponent approach to silica-grafted peptide catalysts : A 3 D continuous-flow organocatalytic system with on-line monitoring of conversion and stereo-selectivity. 2014. Dissertação (Mestrado em Química) – Universidade Federal de São Carlos, São Carlos, 2014. Disponível em: https://repositorio.ufscar.br/handle/ufscar/8017.https://repositorio.ufscar.br/handle/ufscar/8017The derivatization of organocatalysts with functional appendages suitable to anchor onto solid supports is usually achieved by stepwise syntheses. As an alternative to such a strategy, this work describes a one-pot approach to silylated prolyl-peptide catalysts by a multicomponent reaction that enables the simultaneous incorporation of the catalytic and the heterogenizable (triethoxysilane) moieties. A microreactor with high catalytic efficacy and reproducibly in the conjugate addition of aldehydes to nitroolefins was obtained by grafting onto HPLC-grade silica (10 μm) and packing into a column with a selected catalyst. A 3 D continuous-flow system that includes the on-line monitoring of the reaction outcome was set up. For that, the microreactor was coupled to a chromatographic column for the separation of the remaining substrates from the Michael adduct in the second dimension, followed by a chiral polysaccharide column for the analysis of conversion and stereoselectivity. This approach represents a new instrumental setup that combines the advantages of multidimensional chromatography and flow catalysis.A derivação de Organocatalisadores com apêndices funcionais adequados para ancorar em suportes sólidos é geralmente obtida por síntese “passo a passo”. Como uma alternativa para tal estratégia, este trabalho descreve uma abordagem de síntese one-pot de catalisadores prolil-peptio sililados através de uma reação multicomponentes, que permite a incorporação simultânea do sítio catalítico e o grupo funcional de ancoragem (trietoxisilano). Um micro-reactor foi obtido, tendo elevada eficácia catalítica e reprodutibilidade, na adição conjugada de aldeídos a nitro-olefinas, enxertando sobre sílica de grau HPLC (10 um) e preenchendo uma coluna com um catalisador escolhido. Um sistema de fluxo contínuo 3D que inclui a monitoração em linha do resultado da reação foi ajustado para cima. Para isso, o micro-reator foi acoplado a uma coluna cromatográfica para a separação dos substratos restantes do aduto de Michael na segunda dimensão, seguido por uma coluna de polissacarídeo quiral para a análise de conversão e estereosselectividade. Essa abordagem representa uma nova configuração do instrumento que combina as vantagens de cromatografia multidimensional e reações catálisadas em fluxo.Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)porUniversidade Federal de São CarlosCâmpus São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarAsymmetric organocatalysisFlow chemistryMulticomponent reactionsMicroreactorCIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICAMulticomponent approach to silica-grafted peptide catalysts : A 3 D continuous-flow organocatalytic system with on-line monitoring of conversion and stereo-selectivityinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisOnline600600c9d783c2-174c-4a51-9643-0e44f6fc9ac9info:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFSCARinstname:Universidade Federal de São Carlos (UFSCAR)instacron:UFSCARORIGINALDissGSS.pdfDissGSS.pdfapplication/pdf6064128https://repositorio.ufscar.br/bitstream/ufscar/8017/1/DissGSS.pdfaf81f62e90cc7d6ef8aaa427b0a06b40MD51TEXTDissGSS.pdf.txtDissGSS.pdf.txtExtracted texttext/plain111715https://repositorio.ufscar.br/bitstream/ufscar/8017/2/DissGSS.pdf.txt19d5df7e3b87ee0c4b02714a293becf8MD52THUMBNAILDissGSS.pdf.jpgDissGSS.pdf.jpgIM Thumbnailimage/jpeg10406https://repositorio.ufscar.br/bitstream/ufscar/8017/3/DissGSS.pdf.jpg85455c69ff50fb5914a82a7bcc44f80bMD53ufscar/80172023-09-18 18:31:02.711oai:repositorio.ufscar.br:ufscar/8017Repositório InstitucionalPUBhttps://repositorio.ufscar.br/oai/requestopendoar:43222023-09-18T18:31:02Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)false |
dc.title.eng.fl_str_mv |
Multicomponent approach to silica-grafted peptide catalysts : A 3 D continuous-flow organocatalytic system with on-line monitoring of conversion and stereo-selectivity |
title |
Multicomponent approach to silica-grafted peptide catalysts : A 3 D continuous-flow organocatalytic system with on-line monitoring of conversion and stereo-selectivity |
spellingShingle |
Multicomponent approach to silica-grafted peptide catalysts : A 3 D continuous-flow organocatalytic system with on-line monitoring of conversion and stereo-selectivity Scatena, Gabriel dos Santos Asymmetric organocatalysis Flow chemistry Multicomponent reactions Microreactor CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA |
title_short |
Multicomponent approach to silica-grafted peptide catalysts : A 3 D continuous-flow organocatalytic system with on-line monitoring of conversion and stereo-selectivity |
title_full |
Multicomponent approach to silica-grafted peptide catalysts : A 3 D continuous-flow organocatalytic system with on-line monitoring of conversion and stereo-selectivity |
title_fullStr |
Multicomponent approach to silica-grafted peptide catalysts : A 3 D continuous-flow organocatalytic system with on-line monitoring of conversion and stereo-selectivity |
title_full_unstemmed |
Multicomponent approach to silica-grafted peptide catalysts : A 3 D continuous-flow organocatalytic system with on-line monitoring of conversion and stereo-selectivity |
title_sort |
Multicomponent approach to silica-grafted peptide catalysts : A 3 D continuous-flow organocatalytic system with on-line monitoring of conversion and stereo-selectivity |
author |
Scatena, Gabriel dos Santos |
author_facet |
Scatena, Gabriel dos Santos |
author_role |
author |
dc.contributor.authorlattes.por.fl_str_mv |
http://lattes.cnpq.br/8122984740392915 |
dc.contributor.author.fl_str_mv |
Scatena, Gabriel dos Santos |
dc.contributor.advisor1.fl_str_mv |
Paixão, Márcio Weber |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/3773908504964104 |
dc.contributor.advisor-co1.fl_str_mv |
Cass, Quezia Bezerra |
dc.contributor.advisor-co1Lattes.fl_str_mv |
http://lattes.cnpq.br/9197210255594409 |
dc.contributor.authorID.fl_str_mv |
4b49e73d-1509-4df2-b64a-be279d36ef4d |
contributor_str_mv |
Paixão, Márcio Weber Cass, Quezia Bezerra |
dc.subject.eng.fl_str_mv |
Asymmetric organocatalysis Flow chemistry Multicomponent reactions Microreactor |
topic |
Asymmetric organocatalysis Flow chemistry Multicomponent reactions Microreactor CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA |
description |
The derivatization of organocatalysts with functional appendages suitable to anchor onto solid supports is usually achieved by stepwise syntheses. As an alternative to such a strategy, this work describes a one-pot approach to silylated prolyl-peptide catalysts by a multicomponent reaction that enables the simultaneous incorporation of the catalytic and the heterogenizable (triethoxysilane) moieties. A microreactor with high catalytic efficacy and reproducibly in the conjugate addition of aldehydes to nitroolefins was obtained by grafting onto HPLC-grade silica (10 μm) and packing into a column with a selected catalyst. A 3 D continuous-flow system that includes the on-line monitoring of the reaction outcome was set up. For that, the microreactor was coupled to a chromatographic column for the separation of the remaining substrates from the Michael adduct in the second dimension, followed by a chiral polysaccharide column for the analysis of conversion and stereoselectivity. This approach represents a new instrumental setup that combines the advantages of multidimensional chromatography and flow catalysis. |
publishDate |
2014 |
dc.date.issued.fl_str_mv |
2014-11-28 |
dc.date.accessioned.fl_str_mv |
2016-10-20T18:49:47Z |
dc.date.available.fl_str_mv |
2016-10-20T18:49:47Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
SCATENA, Gabriel dos Santos. Multicomponent approach to silica-grafted peptide catalysts : A 3 D continuous-flow organocatalytic system with on-line monitoring of conversion and stereo-selectivity. 2014. Dissertação (Mestrado em Química) – Universidade Federal de São Carlos, São Carlos, 2014. Disponível em: https://repositorio.ufscar.br/handle/ufscar/8017. |
dc.identifier.uri.fl_str_mv |
https://repositorio.ufscar.br/handle/ufscar/8017 |
identifier_str_mv |
SCATENA, Gabriel dos Santos. Multicomponent approach to silica-grafted peptide catalysts : A 3 D continuous-flow organocatalytic system with on-line monitoring of conversion and stereo-selectivity. 2014. Dissertação (Mestrado em Química) – Universidade Federal de São Carlos, São Carlos, 2014. Disponível em: https://repositorio.ufscar.br/handle/ufscar/8017. |
url |
https://repositorio.ufscar.br/handle/ufscar/8017 |
dc.language.iso.fl_str_mv |
por |
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600 600 |
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dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de São Carlos Câmpus São Carlos |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química - PPGQ |
dc.publisher.initials.fl_str_mv |
UFSCar |
publisher.none.fl_str_mv |
Universidade Federal de São Carlos Câmpus São Carlos |
dc.source.none.fl_str_mv |
reponame:Repositório Institucional da UFSCAR instname:Universidade Federal de São Carlos (UFSCAR) instacron:UFSCAR |
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Repositório Institucional da UFSCAR |
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