An easy and efficient method to produce gamma-amino alcohols by reduction of beta-enamino ketones

Detalhes bibliográficos
Autor(a) principal: Harris,Maria Inês N. C.
Data de Publicação: 2004
Outros Autores: Braga,Antonio C. H.
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=S0103-50532004000600027
Resumo: Reduction of beta-enamino ketones 2 with NaBH4 in glacial acetic acid gave gamma-amino alcohols 1 in 70% to 98% yield with diastereomeric excesses, preferentially the syn product, from 44% to 90%. The stereochemistry of these compounds was confirmed by analysis of their tetrahydro-1,3-oxazine derivatives 3.
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spelling An easy and efficient method to produce gamma-amino alcohols by reduction of beta-enamino ketonesamino alcoholsenamino ketonesoxazinesstereoselective reductionReduction of beta-enamino ketones 2 with NaBH4 in glacial acetic acid gave gamma-amino alcohols 1 in 70% to 98% yield with diastereomeric excesses, preferentially the syn product, from 44% to 90%. The stereochemistry of these compounds was confirmed by analysis of their tetrahydro-1,3-oxazine derivatives 3.Sociedade Brasileira de Química2004-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532004000600027Journal of the Brazilian Chemical Society v.15 n.6 2004reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532004000600027info:eu-repo/semantics/openAccessHarris,Maria Inês N. C.Braga,Antonio C. H.eng2005-01-24T00:00:00Zoai:scielo:S0103-50532004000600027Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2005-01-24T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv An easy and efficient method to produce gamma-amino alcohols by reduction of beta-enamino ketones
title An easy and efficient method to produce gamma-amino alcohols by reduction of beta-enamino ketones
spellingShingle An easy and efficient method to produce gamma-amino alcohols by reduction of beta-enamino ketones
Harris,Maria Inês N. C.
amino alcohols
enamino ketones
oxazines
stereoselective reduction
title_short An easy and efficient method to produce gamma-amino alcohols by reduction of beta-enamino ketones
title_full An easy and efficient method to produce gamma-amino alcohols by reduction of beta-enamino ketones
title_fullStr An easy and efficient method to produce gamma-amino alcohols by reduction of beta-enamino ketones
title_full_unstemmed An easy and efficient method to produce gamma-amino alcohols by reduction of beta-enamino ketones
title_sort An easy and efficient method to produce gamma-amino alcohols by reduction of beta-enamino ketones
author Harris,Maria Inês N. C.
author_facet Harris,Maria Inês N. C.
Braga,Antonio C. H.
author_role author
author2 Braga,Antonio C. H.
author2_role author
dc.contributor.author.fl_str_mv Harris,Maria Inês N. C.
Braga,Antonio C. H.
dc.subject.por.fl_str_mv amino alcohols
enamino ketones
oxazines
stereoselective reduction
topic amino alcohols
enamino ketones
oxazines
stereoselective reduction
description Reduction of beta-enamino ketones 2 with NaBH4 in glacial acetic acid gave gamma-amino alcohols 1 in 70% to 98% yield with diastereomeric excesses, preferentially the syn product, from 44% to 90%. The stereochemistry of these compounds was confirmed by analysis of their tetrahydro-1,3-oxazine derivatives 3.
publishDate 2004
dc.date.none.fl_str_mv 2004-12-01
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=S0103-50532004000600027
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532004000600027
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532004000600027
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.15 n.6 2004
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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