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Asymmetric neber reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines

2020-04Journal article Restricted access
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dc.contributor.authorAlves, Claudia
dc.contributor.authorGrosso, Carla
dc.contributor.authorBarrulas, Pedro
dc.contributor.authorPaixao, Jose A.
dc.contributor.authorCardoso, Ana L.
dc.contributor.authorBurke, Anthony J.
dc.contributor.authorLemos, Americo
dc.contributor.authorPinho e Melo, Teresa M. V. D.
dc.date.accessioned2021-06-24T11:35:46Z
dc.date.available2021-06-24T11:35:46Z
dc.date.issued2020-04
dc.description.abstractA 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 beta-ketoxime-1H-tetrazoles followed by the Neber reaction, in the presence of chiral organocatalysts. Among the organocatalysts studied a novel thiourea catalyst derived from 6 beta-aminopenicillanic acid afforded excellent enantioselectivities.
dc.description.sponsorshipPortuguese Agency for Scientific Research, 'Fundacao para a Ciencia e a Tecnologia' (FCT) [UID/QUI/00313/2019]
dc.description.sponsorshipFCTPortuguese Foundation for Science and TechnologyEuropean Commission [SFRH/BD/130198/2017]
dc.description.sponsorshipEvora Chemistry Centre (CQE) through the strategic FCT project [Pest-OE/QUI/UI0619/2019]
dc.description.sponsorship[PD/BD/143159/2019]
dc.description.versioninfo:eu-repo/semantics/publishedVersion
dc.identifier.doi10.1055/s-0039-1691533
dc.identifier.issn0936-5214
dc.identifier.urihttp://hdl.handle.net/10400.1/16529
dc.language.isoeng
dc.peerreviewedyes
dc.publisherGEORG THIEME VERLAG KG
dc.subject2H-azirines
dc.subjectasymmetric Neber reaction
dc.subjectorganocatalysis
dc.subjecttetrazoles
dc.subjectthiourea
dc.subject6 beta-aminopenicillanic acid
dc.subject.otherChemistry
dc.titleAsymmetric neber reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage558
oaire.citation.issue6
oaire.citation.startPage553
oaire.citation.titleSynlett
oaire.citation.volume31
person.familyNameLemos
person.givenNameAmerico
person.identifier.ciencia-idA81D-6DC7-31E4
person.identifier.orcid0000-0001-9588-4555
person.identifier.ridB-4892-2008
person.identifier.scopus-author-id11139694000
rcaap.rightsrestrictedAccess
rcaap.typearticle
relation.isAuthorOfPublication70dfe028-027a-4dec-b6e3-1a49c9be9e60
relation.isAuthorOfPublication.latestForDiscovery70dfe028-027a-4dec-b6e3-1a49c9be9e60

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