Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone

Detalhes bibliográficos
Autor(a) principal: Amongero,Marcela
Data de Publicação: 2010
Outros Autores: Visnovezky,Damian, Kaufman,Teodoro S.
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=S0103-50532010000600011
Resumo: The synthesis of a series of chiral secondary alcohols derived from (R)-carvone, and the stereochemical outcome of their reaction with (±)-ibuprofen, is reported. The racemic drug was transformed into the corresponding diastereomeric esters mediated by DCC/DMAP, affording up to 5.7:1 diastereomeric ratios of the esters derived from either (S)- or (R)-ibuprofen, depending on the type of chiral auxiliary employed.
id SBQ-2_ece86ab84e37850ffb9484a4bff458f3
oai_identifier_str oai:scielo:S0103-50532010000600011
network_acronym_str SBQ-2
network_name_str Journal of the Brazilian Chemical Society (Online)
repository_id_str
spelling Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvoneibuprofencarvoneSteglich esterificationchiral auxiliarieschiral secondary alcoholsThe synthesis of a series of chiral secondary alcohols derived from (R)-carvone, and the stereochemical outcome of their reaction with (±)-ibuprofen, is reported. The racemic drug was transformed into the corresponding diastereomeric esters mediated by DCC/DMAP, affording up to 5.7:1 diastereomeric ratios of the esters derived from either (S)- or (R)-ibuprofen, depending on the type of chiral auxiliary employed.Sociedade Brasileira de Química2010-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000600011Journal of the Brazilian Chemical Society v.21 n.6 2010reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532010000600011info:eu-repo/semantics/openAccessAmongero,MarcelaVisnovezky,DamianKaufman,Teodoro S.eng2010-07-19T00:00:00Zoai:scielo:S0103-50532010000600011Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2010-07-19T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone
title Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone
spellingShingle Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone
Amongero,Marcela
ibuprofen
carvone
Steglich esterification
chiral auxiliaries
chiral secondary alcohols
title_short Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone
title_full Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone
title_fullStr Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone
title_full_unstemmed Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone
title_sort Chiral auxiliary-mediated enantioenrichment of (±)-ibuprofen, under steglich conditions, with secondary alcohols derived from (R)-carvone
author Amongero,Marcela
author_facet Amongero,Marcela
Visnovezky,Damian
Kaufman,Teodoro S.
author_role author
author2 Visnovezky,Damian
Kaufman,Teodoro S.
author2_role author
author
dc.contributor.author.fl_str_mv Amongero,Marcela
Visnovezky,Damian
Kaufman,Teodoro S.
dc.subject.por.fl_str_mv ibuprofen
carvone
Steglich esterification
chiral auxiliaries
chiral secondary alcohols
topic ibuprofen
carvone
Steglich esterification
chiral auxiliaries
chiral secondary alcohols
description The synthesis of a series of chiral secondary alcohols derived from (R)-carvone, and the stereochemical outcome of their reaction with (±)-ibuprofen, is reported. The racemic drug was transformed into the corresponding diastereomeric esters mediated by DCC/DMAP, affording up to 5.7:1 diastereomeric ratios of the esters derived from either (S)- or (R)-ibuprofen, depending on the type of chiral auxiliary employed.
publishDate 2010
dc.date.none.fl_str_mv 2010-01-01
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=S0103-50532010000600011
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000600011
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532010000600011
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.21 n.6 2010
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_ 1750318171032649728

Registros relacionados