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

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dc.citation.firstpage5202
dc.citation.issueNumber16
dc.citation.journalTitleJournal of the American Chemical Society
dc.citation.lastpage5205
dc.citation.volumeNumber138
dc.contributor.authorWang, Jin-Zheng
dc.contributor.authorZhou, Jin
dc.contributor.authorXu, Chang
dc.contributor.authorSun, Hongbin
dc.contributor.authorKürti, László
dc.contributor.authorXu, Qing-Long
dc.date.accessioned2017-06-15T15:30:09Z
dc.date.available2017-06-15T15:30:09Z
dc.date.issued2016
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.
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.
dc.identifier.doihttp://dx.doi.org/10.1021/jacs.6b01458
dc.identifier.urihttps://hdl.handle.net/1911/94871
dc.language.isoeng
dc.publisherAmerican Chemical Society
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.
dc.titleSymmetry in Cascade Chirality-Transfer Processes: A Catalytic Atroposelective Direct Arylation Approach to BINOL Derivatives
dc.typeJournal article
dc.type.dcmiText
dc.type.publicationpost-print
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