Stereospecific Synthesis of Two Isomers of (4,8) - Dimethyldecanal: The Aggregation Pheromone of Tribolium spp

Detalhes bibliográficos
Autor(a) principal: Zarbin,Paulo H.G.
Data de Publicação: 1998
Outros Autores: Cruz,Wellington de O., Ferreira,J. Tércio B.
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=S0103-50531998000500018
Resumo: A straightforward stereospecific synthesis of two stereoisomers, (4R, 8S) and (4S, 8S), of 4,8-dimethyldecanal (1), out of four possible isomers, is described. The key step employs the coupling reaction of tosylates (3) and (3a), which are obtained from (R)- and (S)- citronellol, with the chiral Grignard reagent prepared from comercial (S)-(+)-1-bromo-2-methylbutane (4).
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spelling Stereospecific Synthesis of Two Isomers of (4,8) - Dimethyldecanal: The Aggregation Pheromone of Tribolium spp4,8-dimethyldecanalTribolium sppasymmetric synthesispheromoneA straightforward stereospecific synthesis of two stereoisomers, (4R, 8S) and (4S, 8S), of 4,8-dimethyldecanal (1), out of four possible isomers, is described. The key step employs the coupling reaction of tosylates (3) and (3a), which are obtained from (R)- and (S)- citronellol, with the chiral Grignard reagent prepared from comercial (S)-(+)-1-bromo-2-methylbutane (4).Sociedade Brasileira de Química1998-09-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531998000500018Journal of the Brazilian Chemical Society v.9 n.5 1998reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50531998000500018info:eu-repo/semantics/openAccessZarbin,Paulo H.G.Cruz,Wellington de O.Ferreira,J. Tércio B.eng2002-11-06T00:00:00Zoai:scielo:S0103-50531998000500018Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2002-11-06T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Stereospecific Synthesis of Two Isomers of (4,8) - Dimethyldecanal: The Aggregation Pheromone of Tribolium spp
title Stereospecific Synthesis of Two Isomers of (4,8) - Dimethyldecanal: The Aggregation Pheromone of Tribolium spp
spellingShingle Stereospecific Synthesis of Two Isomers of (4,8) - Dimethyldecanal: The Aggregation Pheromone of Tribolium spp
Zarbin,Paulo H.G.
4,8-dimethyldecanal
Tribolium spp
asymmetric synthesis
pheromone
title_short Stereospecific Synthesis of Two Isomers of (4,8) - Dimethyldecanal: The Aggregation Pheromone of Tribolium spp
title_full Stereospecific Synthesis of Two Isomers of (4,8) - Dimethyldecanal: The Aggregation Pheromone of Tribolium spp
title_fullStr Stereospecific Synthesis of Two Isomers of (4,8) - Dimethyldecanal: The Aggregation Pheromone of Tribolium spp
title_full_unstemmed Stereospecific Synthesis of Two Isomers of (4,8) - Dimethyldecanal: The Aggregation Pheromone of Tribolium spp
title_sort Stereospecific Synthesis of Two Isomers of (4,8) - Dimethyldecanal: The Aggregation Pheromone of Tribolium spp
author Zarbin,Paulo H.G.
author_facet Zarbin,Paulo H.G.
Cruz,Wellington de O.
Ferreira,J. Tércio B.
author_role author
author2 Cruz,Wellington de O.
Ferreira,J. Tércio B.
author2_role author
author
dc.contributor.author.fl_str_mv Zarbin,Paulo H.G.
Cruz,Wellington de O.
Ferreira,J. Tércio B.
dc.subject.por.fl_str_mv 4,8-dimethyldecanal
Tribolium spp
asymmetric synthesis
pheromone
topic 4,8-dimethyldecanal
Tribolium spp
asymmetric synthesis
pheromone
description A straightforward stereospecific synthesis of two stereoisomers, (4R, 8S) and (4S, 8S), of 4,8-dimethyldecanal (1), out of four possible isomers, is described. The key step employs the coupling reaction of tosylates (3) and (3a), which are obtained from (R)- and (S)- citronellol, with the chiral Grignard reagent prepared from comercial (S)-(+)-1-bromo-2-methylbutane (4).
publishDate 1998
dc.date.none.fl_str_mv 1998-09-01
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=S0103-50531998000500018
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531998000500018
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50531998000500018
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.9 n.5 1998
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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