Symmetry in Cascade Chirality-Transfer Processes: A Catalytic Atroposelective Direct Arylation Approach to BINOL Derivatives

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dc.citation.firstpage5202en_US
dc.citation.issueNumber16en_US
dc.citation.journalTitleJournal of the American Chemical Societyen_US
dc.citation.lastpage5205en_US
dc.citation.volumeNumber138en_US
dc.contributor.authorWang, Jin-Zhengen_US
dc.contributor.authorZhou, Jinen_US
dc.contributor.authorXu, Changen_US
dc.contributor.authorSun, Hongbinen_US
dc.contributor.authorKürti, Lászlóen_US
dc.contributor.authorXu, Qing-Longen_US
dc.date.accessioned2017-06-15T15:30:09Zen_US
dc.date.available2017-06-15T15:30:09Zen_US
dc.date.issued2016en_US
dc.description.abstractHerein we disclose a scalable organocatalytic direct arylation approach for the regio- and atroposelective synthesis of non-C2-symmetric 2,2′-dihydroxy-1,1′-binaphthalenes (BINOLs). In the presence of catalytic amounts of axially chiral phosphoric acids, phenols and naphthols are coupled with iminoquinones via a cascade process that involves sequential aminal formation, sigmatropic rearrangement, and rearomatization to afford enantiomerically enriched BINOL derivatives in good to excellent yields. Our studies suggest that the (local) symmetry of the initially formed aminal intermediate has a dramatic impact on the level of enantioinduction in the final product. Aminals with a plane of symmetry give rise to BINOL derivatives with significantly lower enantiomeric excess than unsymmetrical ones featuring a stereogenic center. Presumably asymmetric induction in the sigmatropic rearrangement step is significantly more challenging than during aminal formation. Sigmatropic rearrangement of the enantiomerically enriched aminal and subsequent rearomatization transfers the central chirality into axial chirality with high fidelity.en_US
dc.identifier.citationWang, Jin-Zheng, Zhou, Jin, Xu, Chang, et al.. "Symmetry in Cascade Chirality-Transfer Processes: A Catalytic Atroposelective Direct Arylation Approach to BINOL Derivatives." <i>Journal of the American Chemical Society,</i> 138, no. 16 (2016) American Chemical Society: 5202-5205. http://dx.doi.org/10.1021/jacs.6b01458.en_US
dc.identifier.doihttp://dx.doi.org/10.1021/jacs.6b01458en_US
dc.identifier.urihttps://hdl.handle.net/1911/94871en_US
dc.language.isoengen_US
dc.publisherAmerican Chemical Societyen_US
dc.rightsThis is an author's peer-reviewed final manuscript, as accepted by the publisher. The published article is copyrighted by the American Chemical Society.en_US
dc.titleSymmetry in Cascade Chirality-Transfer Processes: A Catalytic Atroposelective Direct Arylation Approach to BINOL Derivativesen_US
dc.typeJournal articleen_US
dc.type.dcmiTexten_US
dc.type.publicationpost-printen_US
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