A Straightforward Synthesis of Enantiopure (1S,2R)-Ephenamine

Detalhes bibliográficos
Autor(a) principal: Velho,Arthur C. C.
Data de Publicação: 2020
Outros Autores: Martins,José E. D.
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=S0103-50532020001202462
Resumo: An enantioselective six-step synthesis of (1S,2R)-ephenamine starting from readily available chiral amino acid is disclosed presenting 26% overall yield and high optical purity. The use of chiral phenylglycine as starting material was also studied and did not present satisfactory results due to a very sensitive a-carbonyl/benzylic stereogenic center that, in our hands, led to racemization.
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spelling A Straightforward Synthesis of Enantiopure (1S,2R)-Ephenaminechiral auxiliarychiral amino alcohols(1S,2R)-ephenamineAn enantioselective six-step synthesis of (1S,2R)-ephenamine starting from readily available chiral amino acid is disclosed presenting 26% overall yield and high optical purity. The use of chiral phenylglycine as starting material was also studied and did not present satisfactory results due to a very sensitive a-carbonyl/benzylic stereogenic center that, in our hands, led to racemization.Sociedade Brasileira de Química2020-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020001202462Journal of the Brazilian Chemical Society v.31 n.12 2020reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20200121info:eu-repo/semantics/openAccessVelho,Arthur C. C.Martins,José E. D.eng2020-12-09T00:00:00Zoai:scielo:S0103-50532020001202462Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2020-12-09T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv A Straightforward Synthesis of Enantiopure (1S,2R)-Ephenamine
title A Straightforward Synthesis of Enantiopure (1S,2R)-Ephenamine
spellingShingle A Straightforward Synthesis of Enantiopure (1S,2R)-Ephenamine
Velho,Arthur C. C.
chiral auxiliary
chiral amino alcohols
(1S,2R)-ephenamine
title_short A Straightforward Synthesis of Enantiopure (1S,2R)-Ephenamine
title_full A Straightforward Synthesis of Enantiopure (1S,2R)-Ephenamine
title_fullStr A Straightforward Synthesis of Enantiopure (1S,2R)-Ephenamine
title_full_unstemmed A Straightforward Synthesis of Enantiopure (1S,2R)-Ephenamine
title_sort A Straightforward Synthesis of Enantiopure (1S,2R)-Ephenamine
author Velho,Arthur C. C.
author_facet Velho,Arthur C. C.
Martins,José E. D.
author_role author
author2 Martins,José E. D.
author2_role author
dc.contributor.author.fl_str_mv Velho,Arthur C. C.
Martins,José E. D.
dc.subject.por.fl_str_mv chiral auxiliary
chiral amino alcohols
(1S,2R)-ephenamine
topic chiral auxiliary
chiral amino alcohols
(1S,2R)-ephenamine
description An enantioselective six-step synthesis of (1S,2R)-ephenamine starting from readily available chiral amino acid is disclosed presenting 26% overall yield and high optical purity. The use of chiral phenylglycine as starting material was also studied and did not present satisfactory results due to a very sensitive a-carbonyl/benzylic stereogenic center that, in our hands, led to racemization.
publishDate 2020
dc.date.none.fl_str_mv 2020-12-01
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=S0103-50532020001202462
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020001202462
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.21577/0103-5053.20200121
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.12 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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