Stereoselective Addition of Diethylzinc to Aldehydes Using Chiral β-Hydroxy-2-oxazolines as Catalysts

Detalhes bibliográficos
Autor(a) principal: Marques,Francisco A.
Data de Publicação: 2015
Outros Autores: Wosch,Celso L., Frensch,Gustavo, Labes,Ricardo, Maia,Beatriz H. L. N. S., Salomé,Kahlil S., Barison,Andersson, Guerrero Jr,Palimécio G.
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=S0103-50532015000100165
Resumo: Chiral β-hydroxy-2-oxazolines were synthesized and evaluated as catalysts for the addition of diethylzinc to aldehydes. All oxazolines proved effective in obtaining the addition products. The best enantiomeric excesses (69-78%) were obtained using the chiral β-hydroxy oxazoline derived from (−)-menthone and the amino alcohol 2-amino-2-methylpropan-1-ol.
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spelling Stereoselective Addition of Diethylzinc to Aldehydes Using Chiral β-Hydroxy-2-oxazolines as Catalysts(−)-menthonechiral β-hydroxy-2-oxazolinescatalystsdiethylzincaldehydesChiral β-hydroxy-2-oxazolines were synthesized and evaluated as catalysts for the addition of diethylzinc to aldehydes. All oxazolines proved effective in obtaining the addition products. The best enantiomeric excesses (69-78%) were obtained using the chiral β-hydroxy oxazoline derived from (−)-menthone and the amino alcohol 2-amino-2-methylpropan-1-ol.Sociedade Brasileira de Química2015-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532015000100165Journal of the Brazilian Chemical Society v.26 n.1 2015reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20140233info:eu-repo/semantics/openAccessMarques,Francisco A.Wosch,Celso L.Frensch,GustavoLabes,RicardoMaia,Beatriz H. L. N. S.Salomé,Kahlil S.Barison,AnderssonGuerrero Jr,Palimécio G.eng2015-02-03T00:00:00Zoai:scielo:S0103-50532015000100165Revistahttp://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 Stereoselective Addition of Diethylzinc to Aldehydes Using Chiral β-Hydroxy-2-oxazolines as Catalysts
title Stereoselective Addition of Diethylzinc to Aldehydes Using Chiral β-Hydroxy-2-oxazolines as Catalysts
spellingShingle Stereoselective Addition of Diethylzinc to Aldehydes Using Chiral β-Hydroxy-2-oxazolines as Catalysts
Marques,Francisco A.
(−)-menthone
chiral β-hydroxy-2-oxazolines
catalysts
diethylzinc
aldehydes
title_short Stereoselective Addition of Diethylzinc to Aldehydes Using Chiral β-Hydroxy-2-oxazolines as Catalysts
title_full Stereoselective Addition of Diethylzinc to Aldehydes Using Chiral β-Hydroxy-2-oxazolines as Catalysts
title_fullStr Stereoselective Addition of Diethylzinc to Aldehydes Using Chiral β-Hydroxy-2-oxazolines as Catalysts
title_full_unstemmed Stereoselective Addition of Diethylzinc to Aldehydes Using Chiral β-Hydroxy-2-oxazolines as Catalysts
title_sort Stereoselective Addition of Diethylzinc to Aldehydes Using Chiral β-Hydroxy-2-oxazolines as Catalysts
author Marques,Francisco A.
author_facet Marques,Francisco A.
Wosch,Celso L.
Frensch,Gustavo
Labes,Ricardo
Maia,Beatriz H. L. N. S.
Salomé,Kahlil S.
Barison,Andersson
Guerrero Jr,Palimécio G.
author_role author
author2 Wosch,Celso L.
Frensch,Gustavo
Labes,Ricardo
Maia,Beatriz H. L. N. S.
Salomé,Kahlil S.
Barison,Andersson
Guerrero Jr,Palimécio G.
author2_role author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Marques,Francisco A.
Wosch,Celso L.
Frensch,Gustavo
Labes,Ricardo
Maia,Beatriz H. L. N. S.
Salomé,Kahlil S.
Barison,Andersson
Guerrero Jr,Palimécio G.
dc.subject.por.fl_str_mv (−)-menthone
chiral β-hydroxy-2-oxazolines
catalysts
diethylzinc
aldehydes
topic (−)-menthone
chiral β-hydroxy-2-oxazolines
catalysts
diethylzinc
aldehydes
description Chiral β-hydroxy-2-oxazolines were synthesized and evaluated as catalysts for the addition of diethylzinc to aldehydes. All oxazolines proved effective in obtaining the addition products. The best enantiomeric excesses (69-78%) were obtained using the chiral β-hydroxy oxazoline derived from (−)-menthone and the amino alcohol 2-amino-2-methylpropan-1-ol.
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=S0103-50532015000100165
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532015000100165
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20140233
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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