Studies towards the construction of quaternary indolizidines by [2,3]-sigmatropic rearrangement cocatalyzed by ionic liquid
Autor(a) principal: | |
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Data de Publicação: | 2009 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000500002 |
Resumo: | An efficient enantioselective approach for preparation of quaternary centers from proline 5 building block has been developed through [2,3]-sigmatropic Stevens rearrangement co-catalyzed by ionic liquid. The sigmatropic rearrangement was stereospecific because the [2,3]-migrations were restricted to the same face, and the stereoselectivity arose from the previous N-alkylation step in 8. The approach showed better yields than described in literature. The use of 1-butyl-3-methylimidazolium hexafluorophosphate showed an improvement in the yields of the Stevens rearrangement due to a possible stabilization and/or activatation of zwiterionicspecies in solution by the ionic liquid. Several indolizidine moieties were synthesized from quaternary proline derivative (S)-5. |
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Studies towards the construction of quaternary indolizidines by [2,3]-sigmatropic rearrangement cocatalyzed by ionic liquidStevens rearrangement[2,3]-sigmatropicindolizidinesionic liquidco-catalyzedAn efficient enantioselective approach for preparation of quaternary centers from proline 5 building block has been developed through [2,3]-sigmatropic Stevens rearrangement co-catalyzed by ionic liquid. The sigmatropic rearrangement was stereospecific because the [2,3]-migrations were restricted to the same face, and the stereoselectivity arose from the previous N-alkylation step in 8. The approach showed better yields than described in literature. The use of 1-butyl-3-methylimidazolium hexafluorophosphate showed an improvement in the yields of the Stevens rearrangement due to a possible stabilization and/or activatation of zwiterionicspecies in solution by the ionic liquid. Several indolizidine moieties were synthesized from quaternary proline derivative (S)-5.Sociedade Brasileira de Química2009-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000500002Journal of the Brazilian Chemical Society v.20 n.5 2009reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532009000500002info:eu-repo/semantics/openAccessDuran-Lara,Esteban F.Shankaraiah,NagulaGeraldo,DanielaSantos,Leonardo S.eng2009-06-29T00:00:00Zoai:scielo:S0103-50532009000500002Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2009-06-29T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Studies towards the construction of quaternary indolizidines by [2,3]-sigmatropic rearrangement cocatalyzed by ionic liquid |
title |
Studies towards the construction of quaternary indolizidines by [2,3]-sigmatropic rearrangement cocatalyzed by ionic liquid |
spellingShingle |
Studies towards the construction of quaternary indolizidines by [2,3]-sigmatropic rearrangement cocatalyzed by ionic liquid Duran-Lara,Esteban F. Stevens rearrangement [2,3]-sigmatropic indolizidines ionic liquid co-catalyzed |
title_short |
Studies towards the construction of quaternary indolizidines by [2,3]-sigmatropic rearrangement cocatalyzed by ionic liquid |
title_full |
Studies towards the construction of quaternary indolizidines by [2,3]-sigmatropic rearrangement cocatalyzed by ionic liquid |
title_fullStr |
Studies towards the construction of quaternary indolizidines by [2,3]-sigmatropic rearrangement cocatalyzed by ionic liquid |
title_full_unstemmed |
Studies towards the construction of quaternary indolizidines by [2,3]-sigmatropic rearrangement cocatalyzed by ionic liquid |
title_sort |
Studies towards the construction of quaternary indolizidines by [2,3]-sigmatropic rearrangement cocatalyzed by ionic liquid |
author |
Duran-Lara,Esteban F. |
author_facet |
Duran-Lara,Esteban F. Shankaraiah,Nagula Geraldo,Daniela Santos,Leonardo S. |
author_role |
author |
author2 |
Shankaraiah,Nagula Geraldo,Daniela Santos,Leonardo S. |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Duran-Lara,Esteban F. Shankaraiah,Nagula Geraldo,Daniela Santos,Leonardo S. |
dc.subject.por.fl_str_mv |
Stevens rearrangement [2,3]-sigmatropic indolizidines ionic liquid co-catalyzed |
topic |
Stevens rearrangement [2,3]-sigmatropic indolizidines ionic liquid co-catalyzed |
description |
An efficient enantioselective approach for preparation of quaternary centers from proline 5 building block has been developed through [2,3]-sigmatropic Stevens rearrangement co-catalyzed by ionic liquid. The sigmatropic rearrangement was stereospecific because the [2,3]-migrations were restricted to the same face, and the stereoselectivity arose from the previous N-alkylation step in 8. The approach showed better yields than described in literature. The use of 1-butyl-3-methylimidazolium hexafluorophosphate showed an improvement in the yields of the Stevens rearrangement due to a possible stabilization and/or activatation of zwiterionicspecies in solution by the ionic liquid. Several indolizidine moieties were synthesized from quaternary proline derivative (S)-5. |
publishDate |
2009 |
dc.date.none.fl_str_mv |
2009-01-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000500002 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000500002 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532009000500002 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.20 n.5 2009 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
_version_ |
1750318169840418817 |