Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines

Detalhes bibliográficos
Autor(a) principal: Alves, Cláudia
Data de Publicação: 2019
Outros Autores: Grosso, Carla, Barrulas, Pedro, Paixão, José A., Cardoso, Ana L., Burke, Anthony J., Lemos, Américo, Melo, Teresa M. V. D. Pinho e
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
DOI: 10.1055/s-0039-1691533
Texto Completo: http://hdl.handle.net/10316/90926
https://doi.org/10.1055/s-0039-1691533
Resumo: A successful one-pot methodology for the synthesis of chiral 2-tetrazolyl-2H-azirines has been established, resorting to organocatalysis. The protocol involves the in situ tosylation of β-ketoxime-1H-tetrazoles followed by the Neber reaction, in the presence of chiral organocatalysts. Among the organocatalysts studied a novel thiourea catalyst derived from 6β-aminopenicillanic acid afforded excellent enantioselectivities.
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spelling Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines2H-azirinesAsymmetric Neber reactionOrganocatalysisTetrazolesThiourea6β-aminopenicillanic acidA successful one-pot methodology for the synthesis of chiral 2-tetrazolyl-2H-azirines has been established, resorting to organocatalysis. The protocol involves the in situ tosylation of β-ketoxime-1H-tetrazoles followed by the Neber reaction, in the presence of chiral organocatalysts. Among the organocatalysts studied a novel thiourea catalyst derived from 6β-aminopenicillanic acid afforded excellent enantioselectivities.Georg Thieme Verlag2019info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/90926http://hdl.handle.net/10316/90926https://doi.org/10.1055/s-0039-1691533eng0936-52141437-2096https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0039-1691533Alves, CláudiaGrosso, CarlaBarrulas, PedroPaixão, José A.Cardoso, Ana L.Burke, Anthony J.Lemos, AméricoMelo, Teresa M. V. D. Pinho einfo: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:RCAAP2022-05-25T05:46:49Zoai:estudogeral.uc.pt:10316/90926Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:10:54.671112Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines
title Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines
spellingShingle Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines
Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines
Alves, Cláudia
2H-azirines
Asymmetric Neber reaction
Organocatalysis
Tetrazoles
Thiourea
6β-aminopenicillanic acid
Alves, Cláudia
2H-azirines
Asymmetric Neber reaction
Organocatalysis
Tetrazoles
Thiourea
6β-aminopenicillanic acid
title_short Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines
title_full Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines
title_fullStr Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines
Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines
title_full_unstemmed Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines
Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines
title_sort Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines
author Alves, Cláudia
author_facet Alves, Cláudia
Alves, Cláudia
Grosso, Carla
Barrulas, Pedro
Paixão, José A.
Cardoso, Ana L.
Burke, Anthony J.
Lemos, Américo
Melo, Teresa M. V. D. Pinho e
Grosso, Carla
Barrulas, Pedro
Paixão, José A.
Cardoso, Ana L.
Burke, Anthony J.
Lemos, Américo
Melo, Teresa M. V. D. Pinho e
author_role author
author2 Grosso, Carla
Barrulas, Pedro
Paixão, José A.
Cardoso, Ana L.
Burke, Anthony J.
Lemos, Américo
Melo, Teresa M. V. D. Pinho e
author2_role author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Alves, Cláudia
Grosso, Carla
Barrulas, Pedro
Paixão, José A.
Cardoso, Ana L.
Burke, Anthony J.
Lemos, Américo
Melo, Teresa M. V. D. Pinho e
dc.subject.por.fl_str_mv 2H-azirines
Asymmetric Neber reaction
Organocatalysis
Tetrazoles
Thiourea
6β-aminopenicillanic acid
topic 2H-azirines
Asymmetric Neber reaction
Organocatalysis
Tetrazoles
Thiourea
6β-aminopenicillanic acid
description A successful one-pot methodology for the synthesis of chiral 2-tetrazolyl-2H-azirines has been established, resorting to organocatalysis. The protocol involves the in situ tosylation of β-ketoxime-1H-tetrazoles followed by the Neber reaction, in the presence of chiral organocatalysts. Among the organocatalysts studied a novel thiourea catalyst derived from 6β-aminopenicillanic acid afforded excellent enantioselectivities.
publishDate 2019
dc.date.none.fl_str_mv 2019
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/10316/90926
http://hdl.handle.net/10316/90926
https://doi.org/10.1055/s-0039-1691533
url http://hdl.handle.net/10316/90926
https://doi.org/10.1055/s-0039-1691533
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0936-5214
1437-2096
https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0039-1691533
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Georg Thieme Verlag
publisher.none.fl_str_mv Georg Thieme Verlag
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
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv
_version_ 1822218240717225984
dc.identifier.doi.none.fl_str_mv 10.1055/s-0039-1691533

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