A general method for the synthesis of enantiopure 1,5-amino alcohols

A variety of (R)-phenylglycinol-derived oxazolopiperidone lactams 1-14 were converted to linear-chain enantiopure amino diols 15-26 by reduction with LiNH2BH3 in an unprecedented process involving the simultaneous reductive opening of the oxazolidine and lactam rings. Subsequent removal of the pheny...

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Detalles Bibliográficos
Autores: Guignard, Guillaume Michel Pablo, Llor Brunés, Núria, Urbina Teixidor, Aina, Bosch Cartes, Joan, Amat Tusón, Mercedes
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2016
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/98971
Acceso en línea:https://hdl.handle.net/2445/98971
Access Level:acceso abierto
Palabra clave:Síntesi orgànica
Síntesi asimètrica
Reducció química
Lactames
Organic synthesis
Asymmetric synthesis
Reduction (Chemistry)
Lactams
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repository_id_str
spelling A general method for the synthesis of enantiopure 1,5-amino alcoholsGuignard, Guillaume Michel PabloLlor Brunés, NúriaUrbina Teixidor, AinaBosch Cartes, JoanAmat Tusón, MercedesSíntesi orgànicaSíntesi asimètricaReducció químicaLactamesOrganic synthesisAsymmetric synthesisReduction (Chemistry)LactamsA variety of (R)-phenylglycinol-derived oxazolopiperidone lactams 1-14 were converted to linear-chain enantiopure amino diols 15-26 by reduction with LiNH2BH3 in an unprecedented process involving the simultaneous reductive opening of the oxazolidine and lactam rings. Subsequent removal of the phenylethanol moiety gave enantiopure 5-amino-1-pentanols bearing substituents at the 2-, 3-, 4-, 2,2-, 2,3- 2,4- and 3,4-positions (28-36), which were isolated as their N-Boc derivatives.Wiley-VCH2016201720162016info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion11 p.application/pdfhttps://hdl.handle.net/2445/98971Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésVersió postprint del document publicat a: http://dx.doi.org/10.1002/ejoc.201501409European Journal of Organic Chemistry, 2016, vol. 2016, num. 4, p. 693-703http://dx.doi.org/10.1002/ejoc.201501409(c) Wiley-VCH, 2016info:eu-repo/semantics/openAccessoai:recercat.cat:2445/989712026-05-29T05:05:01Z
dc.title.none.fl_str_mv A general method for the synthesis of enantiopure 1,5-amino alcohols
title A general method for the synthesis of enantiopure 1,5-amino alcohols
spellingShingle A general method for the synthesis of enantiopure 1,5-amino alcohols
Guignard, Guillaume Michel Pablo
Síntesi orgànica
Síntesi asimètrica
Reducció química
Lactames
Organic synthesis
Asymmetric synthesis
Reduction (Chemistry)
Lactams
title_short A general method for the synthesis of enantiopure 1,5-amino alcohols
title_full A general method for the synthesis of enantiopure 1,5-amino alcohols
title_fullStr A general method for the synthesis of enantiopure 1,5-amino alcohols
title_full_unstemmed A general method for the synthesis of enantiopure 1,5-amino alcohols
title_sort A general method for the synthesis of enantiopure 1,5-amino alcohols
dc.creator.none.fl_str_mv Guignard, Guillaume Michel Pablo
Llor Brunés, Núria
Urbina Teixidor, Aina
Bosch Cartes, Joan
Amat Tusón, Mercedes
author Guignard, Guillaume Michel Pablo
author_facet Guignard, Guillaume Michel Pablo
Llor Brunés, Núria
Urbina Teixidor, Aina
Bosch Cartes, Joan
Amat Tusón, Mercedes
author_role author
author2 Llor Brunés, Núria
Urbina Teixidor, Aina
Bosch Cartes, Joan
Amat Tusón, Mercedes
author2_role author
author
author
author
dc.subject.none.fl_str_mv Síntesi orgànica
Síntesi asimètrica
Reducció química
Lactames
Organic synthesis
Asymmetric synthesis
Reduction (Chemistry)
Lactams
topic Síntesi orgànica
Síntesi asimètrica
Reducció química
Lactames
Organic synthesis
Asymmetric synthesis
Reduction (Chemistry)
Lactams
description A variety of (R)-phenylglycinol-derived oxazolopiperidone lactams 1-14 were converted to linear-chain enantiopure amino diols 15-26 by reduction with LiNH2BH3 in an unprecedented process involving the simultaneous reductive opening of the oxazolidine and lactam rings. Subsequent removal of the phenylethanol moiety gave enantiopure 5-amino-1-pentanols bearing substituents at the 2-, 3-, 4-, 2,2-, 2,3- 2,4- and 3,4-positions (28-36), which were isolated as their N-Boc derivatives.
publishDate 2016
dc.date.none.fl_str_mv 2016
2016
2016
2017
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/98971
url https://hdl.handle.net/2445/98971
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: http://dx.doi.org/10.1002/ejoc.201501409
European Journal of Organic Chemistry, 2016, vol. 2016, num. 4, p. 693-703
http://dx.doi.org/10.1002/ejoc.201501409
dc.rights.none.fl_str_mv (c) Wiley-VCH, 2016
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Wiley-VCH, 2016
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 11 p.
application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
dc.source.none.fl_str_mv Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,81155

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