Chiral Amino and Imino-Alcohols Based on (R)-Limonene

Detalhes bibliográficos
Autor(a) principal: Fuscaldo,Rodrigo S.
Data de Publicação: 2020
Outros Autores: Boeira,Eduam O., Stieler,Rafael, Lüdtke,Diogo S., Gregório,José R.
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=S0103-50532020000300438
Resumo: Derivatives of the natural occurring and inexpensive terpene (R) -limonene were synthetized and completely characterized. Starting from internal olefin epoxidation, followed by epoxide opening with sodium azide and azide reduction with LiAlH4, two chiral amino-alcohols were obtained. The amino-alcohols were reacted with three different aldehydes, generating six new imino-alcohols, two of them yielding crystals suitable for X-ray diffraction characterization. The reduction of four of these compounds with LiAlH4 led to new amino-alcohols. All derivatives were obtained with good overall yields through simple reaction protocols.
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spelling Chiral Amino and Imino-Alcohols Based on (R)-Limonenenatural productsNO ligandsSchiff basessustainable chemistryrenewable sourcesDerivatives of the natural occurring and inexpensive terpene (R) -limonene were synthetized and completely characterized. Starting from internal olefin epoxidation, followed by epoxide opening with sodium azide and azide reduction with LiAlH4, two chiral amino-alcohols were obtained. The amino-alcohols were reacted with three different aldehydes, generating six new imino-alcohols, two of them yielding crystals suitable for X-ray diffraction characterization. The reduction of four of these compounds with LiAlH4 led to new amino-alcohols. All derivatives were obtained with good overall yields through simple reaction protocols.Sociedade Brasileira de Química2020-03-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000300438Journal of the Brazilian Chemical Society v.31 n.3 2020reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20190201info:eu-repo/semantics/openAccessFuscaldo,Rodrigo S.Boeira,Eduam O.Stieler,RafaelLüdtke,Diogo S.Gregório,José R.eng2020-02-27T00:00:00Zoai:scielo:S0103-50532020000300438Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2020-02-27T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Chiral Amino and Imino-Alcohols Based on (R)-Limonene
title Chiral Amino and Imino-Alcohols Based on (R)-Limonene
spellingShingle Chiral Amino and Imino-Alcohols Based on (R)-Limonene
Fuscaldo,Rodrigo S.
natural products
N
O ligands
Schiff bases
sustainable chemistry
renewable sources
title_short Chiral Amino and Imino-Alcohols Based on (R)-Limonene
title_full Chiral Amino and Imino-Alcohols Based on (R)-Limonene
title_fullStr Chiral Amino and Imino-Alcohols Based on (R)-Limonene
title_full_unstemmed Chiral Amino and Imino-Alcohols Based on (R)-Limonene
title_sort Chiral Amino and Imino-Alcohols Based on (R)-Limonene
author Fuscaldo,Rodrigo S.
author_facet Fuscaldo,Rodrigo S.
Boeira,Eduam O.
Stieler,Rafael
Lüdtke,Diogo S.
Gregório,José R.
author_role author
author2 Boeira,Eduam O.
Stieler,Rafael
Lüdtke,Diogo S.
Gregório,José R.
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Fuscaldo,Rodrigo S.
Boeira,Eduam O.
Stieler,Rafael
Lüdtke,Diogo S.
Gregório,José R.
dc.subject.por.fl_str_mv natural products
N
O ligands
Schiff bases
sustainable chemistry
renewable sources
topic natural products
N
O ligands
Schiff bases
sustainable chemistry
renewable sources
description Derivatives of the natural occurring and inexpensive terpene (R) -limonene were synthetized and completely characterized. Starting from internal olefin epoxidation, followed by epoxide opening with sodium azide and azide reduction with LiAlH4, two chiral amino-alcohols were obtained. The amino-alcohols were reacted with three different aldehydes, generating six new imino-alcohols, two of them yielding crystals suitable for X-ray diffraction characterization. The reduction of four of these compounds with LiAlH4 led to new amino-alcohols. All derivatives were obtained with good overall yields through simple reaction protocols.
publishDate 2020
dc.date.none.fl_str_mv 2020-03-01
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=S0103-50532020000300438
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000300438
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.21577/0103-5053.20190201
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.31 n.3 2020
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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