Please use this identifier to cite or link to this item: http://hdl.handle.net/2445/142779
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dc.contributor.authorCortes-Clerget, Margery-
dc.contributor.authorJover Modrego, Jesús-
dc.contributor.authorDussart, Jade-
dc.contributor.authorKolodziej, Emilie-
dc.contributor.authorMonteil, Maelle-
dc.contributor.authorMigianu-Griffoni, Evelyne-
dc.contributor.authorGager, Olivier-
dc.contributor.authorDeschamp, Julia-
dc.contributor.authorLecouvey, Marc-
dc.date.accessioned2019-10-22T11:43:43Z-
dc.date.available2019-10-22T11:43:43Z-
dc.date.issued2017-05-11-
dc.identifier.issn0947-6539-
dc.identifier.urihttp://hdl.handle.net/2445/142779-
dc.description.abstractEnamine catalysis is a widespread activation mode in the field of organocatalysis and is often encountered in bifunctional organocatalysts. We previously described H-Pro-Pro-pAla-OMe as a bifunctional catalyst for Michael addition between aldehydes and aromatic nitroalkenes. Considering that opposite selectivities were observed when compared to H-Pro-Pro-Glu-NH2, an analogue described by Wennemers, the activation mode of H-Pro-Pro-pAla-OMe was investigated through kinetic, linear effect studies, NMR analyses, and structural modifications. It appeared that only one bifunctional catalyst was involved in the catalytic cycle, by activating aldehyde through an (E)-enamine and nitroalkene through an acidic interaction. A restrained tripeptide structure was optimal in terms of distance and rigidity for better selectivities and fast reaction rates. Transition-state modeling unveiled the particular selectivity of this phosphonopeptide.-
dc.format.extent9 p.-
dc.format.mimetypeapplication/pdf-
dc.language.isoeng-
dc.publisherWiley-VCH-
dc.relation.isformatofVersió postprint del document publicat a: https://doi.org/10.1002/chem.201700604-
dc.relation.ispartofChemistry-A European Journal, 2017, vol. 23, num. 27, p. 6654-6662-
dc.relation.urihttps://doi.org/10.1002/chem.201700604-
dc.rights(c) Wiley-VCH, 2017-
dc.sourceArticles publicats en revistes (Química Inorgànica i Orgànica)-
dc.subject.classificationReaccions d'addició-
dc.subject.classificationTeoria del funcional de densitat-
dc.subject.classificationCatàlisi-
dc.subject.otherAddition reactions-
dc.subject.otherDensity functionals-
dc.subject.otherCatalysis-
dc.titleBifunctional tripeptide with a phosphonic acid as a bronsted acid for Michael addition: mechanistic insights-
dc.typeinfo:eu-repo/semantics/article-
dc.typeinfo:eu-repo/semantics/acceptedVersion-
dc.identifier.idgrec673706-
dc.date.updated2019-10-22T11:43:43Z-
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess-
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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