Diastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-acetal 1,3-Butadienes with maleimides

Detalhes bibliográficos
Autor(a) principal: Salgueiro, D. A. L.
Data de Publicação: 2012
Outros Autores: Duarte, Vera C. M., Sousa, Cristina, Alves, M. José, Fortes, A. Gil
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/22057
Resumo: Maleimides were combined with D-erythrose benzylidene-acetal 1,3-butadienes 1 and 2 to study the facial selectivity of the Diels-Alder cycloadditions. The selectivity was found to be from moderate to good. The reaction diastereotopicity can be reversed with the temperature. Simultaneous coordination of diene 1, having a free hydroxyl group, and maleimide 3 to a chiral bimetallic Lewis acid catalyst (LACASA-DA reaction) occurs with complete diastereo-control to give a single adduct, using an extra chiral inductor either R- or S-BINOL.
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spelling Diastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-acetal 1,3-Butadienes with maleimidesmaleimidesD-erythrose benzylidene-acetal 1,3-butadieneDiels-Alder cycloadditionselectivityScience & TechnologyMaleimides were combined with D-erythrose benzylidene-acetal 1,3-butadienes 1 and 2 to study the facial selectivity of the Diels-Alder cycloadditions. The selectivity was found to be from moderate to good. The reaction diastereotopicity can be reversed with the temperature. Simultaneous coordination of diene 1, having a free hydroxyl group, and maleimide 3 to a chiral bimetallic Lewis acid catalyst (LACASA-DA reaction) occurs with complete diastereo-control to give a single adduct, using an extra chiral inductor either R- or S-BINOL.Thanks are due to FCT for project funding PTDC/QUI/67407/2006 and FCT and FEDER for funding the NMR spectrometer Bruker Avance III 400 as part of the National NMR Network. V. C. M. D. also thanks for PhD grant (SFRH/BD/61290/2009).Georg Thieme VerlagUniversidade do MinhoSalgueiro, D. A. L.Duarte, Vera C. M.Sousa, CristinaAlves, M. JoséFortes, A. Gil20122012-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/22057eng0936-521410.1055/s-0031-1289785info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:33:15Zoai:repositorium.sdum.uminho.pt:1822/22057Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:28:44.746140Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Diastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-acetal 1,3-Butadienes with maleimides
title Diastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-acetal 1,3-Butadienes with maleimides
spellingShingle Diastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-acetal 1,3-Butadienes with maleimides
Salgueiro, D. A. L.
maleimides
D-erythrose benzylidene-acetal 1,3-butadiene
Diels-Alder cycloaddition
selectivity
Science & Technology
title_short Diastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-acetal 1,3-Butadienes with maleimides
title_full Diastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-acetal 1,3-Butadienes with maleimides
title_fullStr Diastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-acetal 1,3-Butadienes with maleimides
title_full_unstemmed Diastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-acetal 1,3-Butadienes with maleimides
title_sort Diastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-acetal 1,3-Butadienes with maleimides
author Salgueiro, D. A. L.
author_facet Salgueiro, D. A. L.
Duarte, Vera C. M.
Sousa, Cristina
Alves, M. José
Fortes, A. Gil
author_role author
author2 Duarte, Vera C. M.
Sousa, Cristina
Alves, M. José
Fortes, A. Gil
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Salgueiro, D. A. L.
Duarte, Vera C. M.
Sousa, Cristina
Alves, M. José
Fortes, A. Gil
dc.subject.por.fl_str_mv maleimides
D-erythrose benzylidene-acetal 1,3-butadiene
Diels-Alder cycloaddition
selectivity
Science & Technology
topic maleimides
D-erythrose benzylidene-acetal 1,3-butadiene
Diels-Alder cycloaddition
selectivity
Science & Technology
description Maleimides were combined with D-erythrose benzylidene-acetal 1,3-butadienes 1 and 2 to study the facial selectivity of the Diels-Alder cycloadditions. The selectivity was found to be from moderate to good. The reaction diastereotopicity can be reversed with the temperature. Simultaneous coordination of diene 1, having a free hydroxyl group, and maleimide 3 to a chiral bimetallic Lewis acid catalyst (LACASA-DA reaction) occurs with complete diastereo-control to give a single adduct, using an extra chiral inductor either R- or S-BINOL.
publishDate 2012
dc.date.none.fl_str_mv 2012
2012-01-01T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/1822/22057
url http://hdl.handle.net/1822/22057
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0936-5214
10.1055/s-0031-1289785
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Georg Thieme Verlag
publisher.none.fl_str_mv Georg Thieme Verlag
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv
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