N,N-Dialkylhydrazones as Versatile Umpolung Reagents in Enantioselective Anion-Binding Catalysis

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dc.contributor.authorGómez-Martínez, Melania
dc.contributor.authorPérez-Aguilar, María del Carmen
dc.contributor.authorPiekarski, Dariusz Grzegorz
dc.contributor.authorDaniliuc, Constantin D.
dc.contributor.authorGarcía Mancheño, Olga
dc.contributor.organizationOrganic Chemistry Institute, University of Münster, Germanyen
dc.contributor.organizationInstitute of Physical Chemistry, Polish Academy of Sciencesen
dc.date.accessioned2021-12-19T09:44:25Z
dc.date.available2021-12-19T09:44:25Z
dc.date.issued2020-12-11
dc.description.abstractAn enantioselective anion-binding organocatalyticapproach with versatile N,N-dialkylhydrazones (DAHs) aspolarity-reversed (umpolung) nucleophiles is presented. Forthe application of this concept, a highly ordered hydrogen-bond (HB) network between a carefully selected CF3-substi-tuted triazole-based multidentate HB-donor catalyst, the ionicsubstrate and the hydrazone in a supramolecular chiral ion-pair complex was envisioned. The formation of such a networkwas further supported by both experimental and computationalstudies, which showed the crucial role of the anion as a templateunit. The asymmetric Reissert-type reaction of quinolines asa model test reaction chemoselectively delivered highly enan-tiomerically enriched hydrazones (up 95:5 e.r.) that could befurther derivatized to value-added compounds with up to threestereocenters.en
dc.description.sponsorship„This publication is part of a project that has received funding from the European Union’s Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement No. 847413” and “Scientific work published as part of an international co-financed project founded from the programme of the Minister of Science and Higher Education entitled "PMW" in the years 2020 - 2024; agreement no. 5005/H2020-MSCA-COFUND/2019/2”
dc.identifier.citationAngew. Chem.2021,133, 5162 –5167en
dc.identifier.doi10.1002/anie.202013380
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/20818
dc.language.isoen
dc.publisherWiley-VCH on behalf of Chemistry Europeen
dc.relation847413en
dc.rightsDozwolony użytek*
dc.subjectanion-binding catalysisen
dc.subjectasymmetric catalysisen
dc.subjectheterocyclesen
dc.subjecthydrazonesen
dc.subjectumpolungen
dc.titleN,N-Dialkylhydrazones as Versatile Umpolung Reagents in Enantioselective Anion-Binding Catalysisen
dc.typearticleen
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