Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via enantioselective rhodium-catalyzed hydrofunctionalizations of alkynes and allenes

Simple item page
dc.contributor.affiliationUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Molecularesgl
dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Orgánicagl
dc.contributor.authorVelasco Rubio, Álvaro
dc.contributor.authorBernárdez Alfaya, Rodrigo
dc.contributor.authorVarela Carrete, Jesús Ángel
dc.contributor.authorSaá Rodríguez, Carlos
dc.date.accessioned2022-08-08T09:00:19Z
dc.date.available2022-08-08T09:00:19Z
dc.date.issued2021
dc.description.abstractBenzofused seven-membered heterocycles such as 1,4-benzo[e]diazepines (1,4-BZDs) and 1,4-benzo[e]oxazepines (1,4-BZOs) were efficiently synthesized by Rh-catalyzed hydrofunctionalization of internal alkynes and allenes in good to excellent yields. The asymmetric hydroamination of (aminomethyl)anilines gave rise to 3-vinyl-1,4-BZDs with excellent enantioselectivities. Orthogonal N-deprotection of 1,4-BZDs allowed an easy entry to an advanced pyrrolobenzodiazepine metabolite of the V2-receptor antagonist Lixivaptangl
dc.description.peerreviewedSIgl
dc.description.sponsorshipThis work received financial support from MINECO (project CTQ2017-87939-R and ORFEO–CINQA network RED2018-102387-T), the Xunta de Galicia (project ED431C 2018/04 and Centro singular de investigación de Galicia accreditation 2019-2022, ED431G 2019/03), and the European Union (European Regional Development Fund, ERDF). A.V.-R. thanks Xunta de Galicia for a predoctoral fellowship (ED481A-2018/34, 2018-2021)gl
dc.identifier.citationJ. Org. Chem. 2021, 86, 10889−10902. https://doi.org/10.1021/acs.joc.1c01268gl
dc.identifier.doi10.1021/acs.joc.1c01268
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/10347/29033
dc.language.isoenggl
dc.publisherACS Publicationsgl
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-87939-R/ES/NUEVAS RUTAS CATALITICAS A PAHS (HIDROCARBUROS AROMATICOS POLICICLICOS) DOPADOS Y HETEROCICLOS BIOACTIVOSgl
dc.relation.publisherversionhttps://doi.org/10.1021/acs.joc.1c01268gl
dc.rightsAttribution 4.0 International
dc.rights.accessRightsopen accessgl
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subjectAllenesgl
dc.subjectHydrocarbonsgl
dc.subjectLayersgl
dc.subjectLipidsgl
dc.subjectMixturesgl
dc.titleEnantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via enantioselective rhodium-catalyzed hydrofunctionalizations of alkynes and allenesgl
dc.typejournal articlegl
dc.type.hasVersionVoRgl
dspace.entity.typePublication
relation.isAuthorOfPublicatione9be05f9-b5a3-405c-aaf6-4e32700dd21d
relation.isAuthorOfPublication2c024eb2-7698-4785-bd0c-518f70068330
relation.isAuthorOfPublication.latestForDiscoverye9be05f9-b5a3-405c-aaf6-4e32700dd21d

Files

Original bundle

Now showing 1 - 1 of 1
Thumbnail Image
Name:
2021_acs.joc_velasco_enantioenriched.pdf
Size:
1.23 MB
Format:
Adobe Portable Document Format
Description:
Download

Collections

Química Orgánica