A new route to keto and alkyl derivatives of (R)-carvone via diastereoselective conjugate addition of nitronate ions

Detalhes bibliográficos
Autor(a) principal: Costa,Jeronimo S.
Data de Publicação: 2006
Outros Autores: Freire,Bruno S., Moura,André L. S., Pereira,Vera L. Patrocinio
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=S0103-50532006000700006
Resumo: The reactivity and diastereoselectivity of conjugate addition of different nitronates ions to (R)-carvone was systematically studied. The Michael adducts 2a-e were obtained in good yield and 3,2-cis-3,5-trans selectivity. The nitroadducts 2b,c were transformed via Nef reaction into (R)-carvone ketone derivatives 9,10 and nitroadducts 2b,d led to (R)-carvone alkylated derivatives 11,12, via a denitration reaction.
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spelling A new route to keto and alkyl derivatives of (R)-carvone via diastereoselective conjugate addition of nitronate ionsnitroalkyl anionsMichael additionNef reactiontetrabutylammonium fluorideThe reactivity and diastereoselectivity of conjugate addition of different nitronates ions to (R)-carvone was systematically studied. The Michael adducts 2a-e were obtained in good yield and 3,2-cis-3,5-trans selectivity. The nitroadducts 2b,c were transformed via Nef reaction into (R)-carvone ketone derivatives 9,10 and nitroadducts 2b,d led to (R)-carvone alkylated derivatives 11,12, via a denitration reaction.Sociedade Brasileira de Química2006-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532006000700006Journal of the Brazilian Chemical Society v.17 n.7 2006reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532006000700006info:eu-repo/semantics/openAccessCosta,Jeronimo S.Freire,Bruno S.Moura,André L. S.Pereira,Vera L. Patrocinioeng2007-01-29T00:00:00Zoai:scielo:S0103-50532006000700006Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2007-01-29T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv A new route to keto and alkyl derivatives of (R)-carvone via diastereoselective conjugate addition of nitronate ions
title A new route to keto and alkyl derivatives of (R)-carvone via diastereoselective conjugate addition of nitronate ions
spellingShingle A new route to keto and alkyl derivatives of (R)-carvone via diastereoselective conjugate addition of nitronate ions
Costa,Jeronimo S.
nitroalkyl anions
Michael addition
Nef reaction
tetrabutylammonium fluoride
title_short A new route to keto and alkyl derivatives of (R)-carvone via diastereoselective conjugate addition of nitronate ions
title_full A new route to keto and alkyl derivatives of (R)-carvone via diastereoselective conjugate addition of nitronate ions
title_fullStr A new route to keto and alkyl derivatives of (R)-carvone via diastereoselective conjugate addition of nitronate ions
title_full_unstemmed A new route to keto and alkyl derivatives of (R)-carvone via diastereoselective conjugate addition of nitronate ions
title_sort A new route to keto and alkyl derivatives of (R)-carvone via diastereoselective conjugate addition of nitronate ions
author Costa,Jeronimo S.
author_facet Costa,Jeronimo S.
Freire,Bruno S.
Moura,André L. S.
Pereira,Vera L. Patrocinio
author_role author
author2 Freire,Bruno S.
Moura,André L. S.
Pereira,Vera L. Patrocinio
author2_role author
author
author
dc.contributor.author.fl_str_mv Costa,Jeronimo S.
Freire,Bruno S.
Moura,André L. S.
Pereira,Vera L. Patrocinio
dc.subject.por.fl_str_mv nitroalkyl anions
Michael addition
Nef reaction
tetrabutylammonium fluoride
topic nitroalkyl anions
Michael addition
Nef reaction
tetrabutylammonium fluoride
description The reactivity and diastereoselectivity of conjugate addition of different nitronates ions to (R)-carvone was systematically studied. The Michael adducts 2a-e were obtained in good yield and 3,2-cis-3,5-trans selectivity. The nitroadducts 2b,c were transformed via Nef reaction into (R)-carvone ketone derivatives 9,10 and nitroadducts 2b,d led to (R)-carvone alkylated derivatives 11,12, via a denitration reaction.
publishDate 2006
dc.date.none.fl_str_mv 2006-12-01
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=S0103-50532006000700006
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532006000700006
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532006000700006
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.17 n.7 2006
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
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