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Organocatalytic Michael Addition of Unactivated α-Branched Nitroalkanes to Afford Optically Active Tertiary Nitrocompounds

dc.contributor.authorLorea, Beñat
dc.contributor.authorGarcía Urricelqui, Ane
dc.contributor.authorOdriozola, José M.
dc.contributor.authorRazkin, Jesús
dc.contributor.authorEspinal Viguri, Maialen
dc.contributor.authorOyarbide Garmendia, Juan Miguel ORCID
dc.contributor.authorMielgo Vicente, María Antonia ORCID
dc.contributor.authorGarcía, Jesús M.
dc.contributor.authorPalomo Nicolau, Claudio
dc.date.accessioned2024-01-31T18:55:50Z
dc.date.available2024-01-31T18:55:50Z
dc.date.issued2023-11-27
dc.identifier.citationOrganic Letters 25(48) : 8590-8595 (2023)es_ES
dc.identifier.issn1523-7060
dc.identifier.urihttp://hdl.handle.net/10810/64520
dc.description.abstractThe direct, asymmetric conjugate addition of unactivated α-branched nitroalkanes is developed based on the combined use of chiral amine/ureidoaminal bifunctional catalysts and a tunable acrylate template to provide tertiary nitrocompounds in 55–80% isolated yields and high enantioselectivity (e.r. up to 96:4). Elaboration of the ketol moiety in thus obtained adducts allows a fast entry to not only carboxylic and aldehyde derivatives but also nitrile compounds and enantioenriched 5,5-disubstituted γ-lactams.es_ES
dc.description.sponsorshipWe thank the Basque Government (EJ, grant IT1583-22) and Agencia Estatal de Investigación (grants PID2019-109633GB and PID2022-137153NB-C21/AEI/10.13039/501100011033) for financial support. A.G.-U. thanks EJ; B.L. thanks the Navarra Government, and M.E.-V. thanks UPNA (PJUPNA18-2022). Authors also thank SGIker (UPV/EHU/ERDF, EU) for providing NMR, HRMS, and X-ray resources.es_ES
dc.language.isoenges_ES
dc.publisherACSes_ES
dc.relationinfo:eu-repo/grantAgreement/MICINN/PID2019-109633GBes_ES
dc.relationinfo:eu-repo/grantAgreement/MICINN/PID2022-137153NB-C21es_ES
dc.rightsinfo:eu-repo/semantics/openAccesses_ES
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.titleOrganocatalytic Michael Addition of Unactivated α-Branched Nitroalkanes to Afford Optically Active Tertiary Nitrocompoundses_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.rights.holder© 2023 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0.es_ES
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/acs.orglett.3c03340es_ES
dc.identifier.doi10.1021/acs.orglett.3c03340
dc.departamentoesQuímica orgánica Ies_ES
dc.departamentoeuKimika organikoa Ies_ES


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© 2023 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0.
Except where otherwise noted, this item's license is described as © 2023 The Authors. Published by American Chemical Society. This publication is licensed under CC-BY 4.0.