Asymmetric Fe II -Catalyzed Thia-Michael addition reaction to α,β-unsaturated Oxazolidin-2-one Derivatives

DC FieldValueLanguage
dc.contributor.authorLauzon, Samuel-
dc.contributor.authorKeipour, Hoda-
dc.contributor.authorGandon, Vincent-
dc.contributor.authorOllevier, Thierry-
dc.date.accessioned2018-02-19T18:41:29Z-
dc.date.available2018-11-20T00:00:00Z-
dc.date.issued2017-11-20-
dc.identifier.issn15237052fr
dc.identifier.urihttp://hdl.handle.net/20.500.11794/17142-
dc.description.abstractA highly enantioselective FeII-catalyzed thia-Michael addition to α,β‑unsaturated carbonyl derivatives was developed. The scope of the reaction was demonstrated with a selection of aromatic, heterocyclic and aliphatic thiols, and various Michael acceptors. The corresponding β-thioethers were obtained in good to excellent yields (up to 98%) and moderate to excellent enantioselectivities (up to 96:4 er). Unusual hepta-coordination of the metal and chelation to α,β-unsaturated oxazolidin-2-one derivatives allowed the construction of a coherent model rationalizing the enantioselective event. DFT calculations support the proposed model for observed stereoselectivities.fr
dc.languageengfr
dc.publisherAmerican Chemical Societyfr
dc.titleAsymmetric Fe II -Catalyzed Thia-Michael addition reaction to α,β-unsaturated Oxazolidin-2-one Derivativesfr
dc.typeCOAR1_1::Texte::Périodique::Revue::Contribution à un journal::Article::Article de recherchefr
dcterms.bibliographicCitationOrganic letters, Vol. 19 (23), 6324-6327 (2017)fr
dc.identifier.doi10.1021/acs.orglett.7b03118fr
dc.subject.rvmCatalyse énantiosélectivefr
dc.subject.rvmFerfr
dc.subject.rvmComposés carbonylésfr
dc.subject.rvmThiolsfr
rioxxterms.versionAccepted Manuscriptfr
rioxxterms.version_of_recordhttps://doi.org/10.1021/acs.orglett.7b03118fr
rioxxterms.project.funder_nameNatural Sciences and Engineering Research Council of Canadafr
rioxxterms.project.funder_nameCentre in Green Chemistry and Catalysis (CGCC)fr
bul.rights.periodeEmbargo12 moisfr
dc.audience.peerreviewOuifr
Collection:Articles publiés dans des revues avec comité de lecture

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