Publicação
Diastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-acetal 1,3-Butadienes with maleimides
| 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. |
|---|---|
| Autores principais: | Salgueiro, D. A. L. |
| Outros Autores: | Duarte, Vera C. M.; Sousa, Cristina; Alves, M. José; Fortes, A. Gil |
| Assunto: | maleimides D-erythrose benzylidene-acetal 1,3-butadiene Diels-Alder cycloaddition selectivity |
| Ano: | 2012 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| _version_ | 1867439138741944320 |
|---|---|
| author | Salgueiro, D. A. L. |
| author2 | Duarte, Vera C. M. Sousa, Cristina Alves, M. José Fortes, A. Gil |
| author2_role | author author author author |
| author_facet | Salgueiro, D. A. L. Duarte, Vera C. M. Sousa, Cristina Alves, M. José Fortes, A. Gil |
| author_role | author |
| contributor_name_str_mv | RepositóriUM - Universidade do Minho |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Salgueiro, D. A. L.\"},{\"Person.name\":\"Duarte, Vera C. M.\"},{\"Person.name\":\"Sousa, Cristina\"},{\"Person.name\":\"Alves, M. José\"},{\"Person.name\":\"Fortes, A. Gil\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | RepositóriUM - Universidade do Minho |
| datacite.creators.creator.creatorName.fl_str_mv | Salgueiro, D. A. L. Duarte, Vera C. M. Sousa, Cristina Alves, M. José Fortes, A. Gil |
| datacite.date.Accepted.fl_str_mv | 2012-01-01T00:00:00Z |
| datacite.date.available.fl_str_mv | 2012-12-21T18:24:28Z |
| datacite.date.embargoed.fl_str_mv | 2012-12-21T18:24:28Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | maleimides D-erythrose benzylidene-acetal 1,3-butadiene Diels-Alder cycloaddition selectivity |
| datacite.titles.title.fl_str_mv | Diastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-acetal 1,3-Butadienes with maleimides |
| dc.contributor.none.fl_str_mv | RepositóriUM - Universidade do Minho |
| dc.creator.none.fl_str_mv | Salgueiro, D. A. L. Duarte, Vera C. M. Sousa, Cristina Alves, M. José Fortes, A. Gil |
| dc.date.Accepted.fl_str_mv | 2012-01-01T00:00:00Z |
| dc.date.available.fl_str_mv | 2012-12-21T18:24:28Z |
| dc.date.embargoed.fl_str_mv | 2012-12-21T18:24:28Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | https://hdl.handle.net/1822/22057 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Georg Thieme Verlag |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.subject.none.fl_str_mv | maleimides D-erythrose benzylidene-acetal 1,3-butadiene Diels-Alder cycloaddition selectivity |
| dc.title.fl_str_mv | Diastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-acetal 1,3-Butadienes with maleimides |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| 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. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | article |
| fulltext.url.fl_str_mv | https://repositorium.uminho.pt/bitstreams/35e62a9b-523a-48d1-bec6-11953b70ee93/download |
| id | rum_1dafe00601df96feff436c0e082c2f71 |
| identifier.url.fl_str_mv | https://hdl.handle.net/1822/22057 |
| instacron_str | repositorium |
| institution | Universidade do Minho |
| instname_str | Universidade do Minho |
| language | eng |
| network_acronym_str | rum |
| network_name_str | RepositóriUM - Universidade do Minho |
| oai_identifier_str | oai:repositorium.uminho.pt:1822/22057 |
| organization_str_mv | urn:organizationAcronym:repositorium |
| person_str_mv | Salgueiro, D. A. L. Duarte, Vera C. M. Sousa, Cristina Alves, M. José Fortes, A. Gil |
| publishDate | 2012 |
| publisher.none.fl_str_mv | Georg Thieme Verlag |
| reponame_str | RepositóriUM - Universidade do Minho |
| repository_id_str | urn:repositoryAcronym:rum |
| service_str_mv | urn:repositoryAcronym:rum |
| spelling | engGeorg Thieme VerlagMaleimides 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.application/pdfporDiastereo-selectivity in diels–alder cycloadditions of erythrose benzylidene-acetal 1,3-Butadienes with maleimidesSalgueiro, D. A. L.Duarte, Vera C. M.Sousa, CristinaAlves, M. JoséFortes, A. GilHostingInstitutionOrganizationalRepositóriUM - Universidade do Minhoe-mailmailto:repositorium@usdb.uminho.ptrepositorium@usdb.uminho.ptISSNIsPartOf0936-5214DOIIsPartOf10.1055/s-0031-12897852012-12-21T18:24:28Z20122012-01-01T00:00:00ZHandlehttps://hdl.handle.net/1822/22057http://purl.org/coar/access_right/c_abf2open accessmaleimidesD-erythrose benzylidene-acetal 1,3-butadieneDiels-Alder cycloadditionselectivity331330 bytesliteraturehttp://purl.org/coar/resource_type/c_6501journal articlehttp://purl.org/coar/access_right/c_abf2application/pdffulltexthttps://repositorium.uminho.pt/bitstreams/35e62a9b-523a-48d1-bec6-11953b70ee93/download |
| 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 |
| status | SINGLETON |
| subject.fl_str_mv | maleimides D-erythrose benzylidene-acetal 1,3-butadiene Diels-Alder cycloaddition selectivity |
| title | 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_short | 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 |
| topic | maleimides D-erythrose benzylidene-acetal 1,3-butadiene Diels-Alder cycloaddition selectivity |
| topic_facet | maleimides D-erythrose benzylidene-acetal 1,3-butadiene Diels-Alder cycloaddition selectivity |
| url | https://hdl.handle.net/1822/22057 |
| visible | 1 |