A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin

Detalhes bibliográficos
Autor(a) principal: Burke, Anthony J
Data de Publicação: 2017
Outros Autores: Benaglia, Maurizio, Brenna, Davide, Pirola, Margherita, Raimondi, Laura
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10174/22351
https://doi.org/10.1016/j.bmc.2017.01.023
Resumo: The diastereoselective, trichlorosilane-mediate reduction of imines, bearing different and removable chiral auxiliaries, in combination either with achiral bases or catalytic amounts of chiral Lewis bases, was investigated to afford immediate precursors of chiral APIs (Active Pharmaceutical Ingredients). The carbon-nitrogen double bond reduction was successfully performed in batch and in flow mode, in high yields and almost complete stereocontrol. By this metal-free approach, the formal synthesis of rasagiline and tamsulosin was successfully accomplished in micro(meso) flow reactors, under continuous flow conditions. The results of these explorative studies represent a new, important step towards the development of automated processes for the preparation of enantiopure biologically active compounds
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spelling A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosinFlow ChemistryActive Pharmaceutical ingredientThe diastereoselective, trichlorosilane-mediate reduction of imines, bearing different and removable chiral auxiliaries, in combination either with achiral bases or catalytic amounts of chiral Lewis bases, was investigated to afford immediate precursors of chiral APIs (Active Pharmaceutical Ingredients). The carbon-nitrogen double bond reduction was successfully performed in batch and in flow mode, in high yields and almost complete stereocontrol. By this metal-free approach, the formal synthesis of rasagiline and tamsulosin was successfully accomplished in micro(meso) flow reactors, under continuous flow conditions. The results of these explorative studies represent a new, important step towards the development of automated processes for the preparation of enantiopure biologically active compoundsElsevier2018-02-19T16:15:21Z2018-02-192017-12-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10174/22351https://doi.org/10.1016/j.bmc.2017.01.023http://hdl.handle.net/10174/22351https://doi.org/10.1016/j.bmc.2017.01.023eng6242-62470968-089625Bioorganic Medicinal Chemistry23ajb@uevora.ptndndndndA stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosinBurke, Anthony JBenaglia, MaurizioBrenna, DavidePirola, MargheritaRaimondi, Laurainfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-08-08T04:28:44ZPortal AgregadorONG
dc.title.none.fl_str_mv A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin
title A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin
spellingShingle A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin
Burke, Anthony J
Flow Chemistry
Active Pharmaceutical ingredient
title_short A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin
title_full A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin
title_fullStr A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin
title_full_unstemmed A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin
title_sort A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin
author Burke, Anthony J
author_facet Burke, Anthony J
Benaglia, Maurizio
Brenna, Davide
Pirola, Margherita
Raimondi, Laura
author_role author
author2 Benaglia, Maurizio
Brenna, Davide
Pirola, Margherita
Raimondi, Laura
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Burke, Anthony J
Benaglia, Maurizio
Brenna, Davide
Pirola, Margherita
Raimondi, Laura
dc.subject.por.fl_str_mv Flow Chemistry
Active Pharmaceutical ingredient
topic Flow Chemistry
Active Pharmaceutical ingredient
description The diastereoselective, trichlorosilane-mediate reduction of imines, bearing different and removable chiral auxiliaries, in combination either with achiral bases or catalytic amounts of chiral Lewis bases, was investigated to afford immediate precursors of chiral APIs (Active Pharmaceutical Ingredients). The carbon-nitrogen double bond reduction was successfully performed in batch and in flow mode, in high yields and almost complete stereocontrol. By this metal-free approach, the formal synthesis of rasagiline and tamsulosin was successfully accomplished in micro(meso) flow reactors, under continuous flow conditions. The results of these explorative studies represent a new, important step towards the development of automated processes for the preparation of enantiopure biologically active compounds
publishDate 2017
dc.date.none.fl_str_mv 2017-12-01T00:00:00Z
2018-02-19T16:15:21Z
2018-02-19
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10174/22351
https://doi.org/10.1016/j.bmc.2017.01.023
http://hdl.handle.net/10174/22351
https://doi.org/10.1016/j.bmc.2017.01.023
url http://hdl.handle.net/10174/22351
https://doi.org/10.1016/j.bmc.2017.01.023
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 6242-6247
0968-0896
25
Bioorganic Medicinal Chemistry
23
ajb@uevora.pt
nd
nd
nd
nd
A stereoselective, catalytic strategy for the in-flow synthesis of advanced precursors of rasagiline and tamsulosin
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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