A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids

Detalhes bibliográficos
Autor(a) principal: Carmona,Rafaela C.
Data de Publicação: 2015
Outros Autores: Wendler,Edison P., Sakae,George H., Comasseto,João V., Santos,Alcindo A. Dos
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=S0103-50532015000100117
Resumo: A number of aldehydes, alkynols and benzylamines were submitted to A3-coupling reaction, under CuCl catalysis, giving strategically functionalized hydroxy-propargylamines. The procedure allows the use of alkyl as well as aryl aldehydes. Representative substrates were converted into fiveand six-membered cyclic alkaloids by sequential one-pot N-debenzylation/triple bond reduction promoted by Pd, followed by a Mitsunobu-type cyclization.
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spelling A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloidshydroxy-propargylaminesA3-couplingC–H activationcyclic alkaloidsA number of aldehydes, alkynols and benzylamines were submitted to A3-coupling reaction, under CuCl catalysis, giving strategically functionalized hydroxy-propargylamines. The procedure allows the use of alkyl as well as aryl aldehydes. Representative substrates were converted into fiveand six-membered cyclic alkaloids by sequential one-pot N-debenzylation/triple bond reduction promoted by Pd, followed by a Mitsunobu-type cyclization.Sociedade Brasileira de Química2015-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532015000100117Journal of the Brazilian Chemical Society v.26 n.1 2015reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20140223info:eu-repo/semantics/openAccessCarmona,Rafaela C.Wendler,Edison P.Sakae,George H.Comasseto,João V.Santos,Alcindo A. Doseng2015-02-03T00:00:00Zoai:scielo:S0103-50532015000100117Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2015-02-03T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids
title A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids
spellingShingle A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids
Carmona,Rafaela C.
hydroxy-propargylamines
A3-coupling
C–H activation
cyclic alkaloids
title_short A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids
title_full A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids
title_fullStr A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids
title_full_unstemmed A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids
title_sort A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids
author Carmona,Rafaela C.
author_facet Carmona,Rafaela C.
Wendler,Edison P.
Sakae,George H.
Comasseto,João V.
Santos,Alcindo A. Dos
author_role author
author2 Wendler,Edison P.
Sakae,George H.
Comasseto,João V.
Santos,Alcindo A. Dos
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Carmona,Rafaela C.
Wendler,Edison P.
Sakae,George H.
Comasseto,João V.
Santos,Alcindo A. Dos
dc.subject.por.fl_str_mv hydroxy-propargylamines
A3-coupling
C–H activation
cyclic alkaloids
topic hydroxy-propargylamines
A3-coupling
C–H activation
cyclic alkaloids
description A number of aldehydes, alkynols and benzylamines were submitted to A3-coupling reaction, under CuCl catalysis, giving strategically functionalized hydroxy-propargylamines. The procedure allows the use of alkyl as well as aryl aldehydes. Representative substrates were converted into fiveand six-membered cyclic alkaloids by sequential one-pot N-debenzylation/triple bond reduction promoted by Pd, followed by a Mitsunobu-type cyclization.
publishDate 2015
dc.date.none.fl_str_mv 2015-01-01
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=S0103-50532015000100117
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532015000100117
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20140223
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.26 n.1 2015
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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