Atroposelective Silylation of 1,1′‐Biaryl‐2,6‐diols by a Chiral Counteranion Directed Desymmetrization Enhanced by a Subsequent Kinetic Resolution

dc.contributor.authorZhu, Min
dc.contributor.authorJiang, Hua‐Jie
dc.contributor.authorSharanov, Illia
dc.contributor.authorIrran, Elisabeth
dc.contributor.authorOestreich, Martin
dc.date.accessioned2023-07-21T14:01:12Z
dc.date.available2023-07-21T14:01:12Z
dc.date.issued2023-05-22
dc.date.updated2023-07-19T09:02:06Z
dc.description.abstractA desymmetrizing silylation of aromatic diols is reported. The previously unknown asymmetric silyl ether formation of phenol derivatives is achieved by applying List's counteranion directed silylation technique. A silylium-ion-like silicon electrophile generated from an allylic silane paired with an imidodiphosphorimidate (IDPi) enables enantioselective discrimination of achiral 1,1′-biaryl-2,6-diols. The enantioselectivity of that desymmetrization is further improved by a downstream kinetic resolution, converting the monosilylated minor enantiomer into the corresponding, again achiral bissilylated diol.en
dc.description.sponsorshipTU Berlin, Open-Access-Mittel – 2023
dc.identifier.eissn1521-3773
dc.identifier.issn1433-7851
dc.identifier.urihttps://depositonce.tu-berlin.de/handle/11303/19603
dc.identifier.urihttps://doi.org/10.14279/depositonce-18402
dc.language.isoen
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subject.ddc500 Naturwissenschaften und Mathematik::540 Chemie::540 Chemie und zugeordnete Wissenschaften
dc.subject.otheratropisomerismen
dc.subject.otherdesymmetrizationen
dc.subject.otherkinetic resolutionen
dc.subject.otherorganocatalysisen
dc.subject.othersilylium Ionsen
dc.titleAtroposelective Silylation of 1,1′‐Biaryl‐2,6‐diols by a Chiral Counteranion Directed Desymmetrization Enhanced by a Subsequent Kinetic Resolutionen
dc.typeArticle
dc.type.versionpublishedVersion
dcterms.bibliographicCitation.articlenumbere2023044
dcterms.bibliographicCitation.doi10.1002/anie.202304475
dcterms.bibliographicCitation.issue27
dcterms.bibliographicCitation.journaltitleAngewandte Chemie International Editionen
dcterms.bibliographicCitation.originalpublishernameWiley-VCH
dcterms.bibliographicCitation.originalpublisherplaceWeinheim
dcterms.bibliographicCitation.pageend
dcterms.bibliographicCitation.pagestart
dcterms.bibliographicCitation.volume62
dcterms.rightsHolder.referenceCreative-Commons-Lizenz
tub.accessrights.dnbfree
tub.affiliationFak. 2 Mathematik und Naturwissenschaften::Inst. Chemie::FG Organische Chemie / Synthese und Katalyse
tub.publisher.universityorinstitutionTechnische Universität Berlin

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