The Two Faces of Carbenium Ions: Intermolecular Trapping of Prochiral Carbocations with Stereocontrol

dc.contributor.authorWolff, Benedikt
dc.contributor.authorOestreich, Martin
dc.date.accessioned2023-11-08T16:30:42Z
dc.date.available2023-11-08T16:30:42Z
dc.date.issued2023-05-22
dc.date.updated2023-10-16T08:15:08Z
dc.description.abstractCarbenium ions had been suspected and subsequently shown to be key intermediates of a large family of cationic transformations. An enormous body of work is dedicated to their characterization and various roles in reaction mechanisms, e. g. the S<sub>N</sub>1 reaction. Far less attention has been paid to their engagement in asymmetric synthesis and indeed, the differentiation of the diastereo‐ or even enantiotopic faces of structurally unbiased, non‐heteroatom‐stabilized carbenium ions is a daunting challenge. This Review summarizes the approaches taken to achieve the stereoselective addition of nucleophiles to these fleeting intermediates, including recent advances where non‐covalent interactions and chiral counterions are employed to discriminate either side of a trigonal‐planar carbenium ion bearing three different substituents.en
dc.description.sponsorshipTU Berlin, Open-Access-Mittel – 2023
dc.identifier.eissn1869-5868
dc.identifier.issn0021-2148
dc.identifier.urihttps://depositonce.tu-berlin.de/handle/11303/20263
dc.identifier.urihttps://doi.org/10.14279/depositonce-19061
dc.language.isoen
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subject.ddc500 Naturwissenschaften und Mathematik::540 Chemie::547 Organische Chemie
dc.subject.othercarbocations
dc.subject.otherchiral anions
dc.subject.otherdiastereoselectivity
dc.subject.otherenantioselectivity
dc.subject.otherSN1 reaction
dc.titleThe Two Faces of Carbenium Ions: Intermolecular Trapping of Prochiral Carbocations with Stereocontrolen
dc.typeArticle
dc.type.versionpublishedVersion
dcterms.bibliographicCitation.articlenumbere202300027
dcterms.bibliographicCitation.doi10.1002/ijch.202300027
dcterms.bibliographicCitation.issue7-8
dcterms.bibliographicCitation.journaltitleIsrael Journal of Chemistryen
dcterms.bibliographicCitation.originalpublishernameWiley-VCH
dcterms.bibliographicCitation.originalpublisherplaceWeinheim
dcterms.bibliographicCitation.pageend
dcterms.bibliographicCitation.pagestart
dcterms.bibliographicCitation.volume63
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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