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dc.contributor.authorWang, Jin-Zheng
Zhou, Jin
Xu, Chang
Sun, Hongbin
Kürti, László
Xu, Qing-Long
dc.date.accessioned 2017-06-15T15:30:09Z
dc.date.available 2017-06-15T15:30:09Z
dc.date.issued 2016
dc.identifier.citation Wang, Jin-Zheng, Zhou, Jin, Xu, Chang, et al.. "Symmetry in Cascade Chirality-Transfer Processes: A Catalytic Atroposelective Direct Arylation Approach to BINOL Derivatives." Journal of the American Chemical Society, 138, no. 16 (2016) American Chemical Society: 5202-5205. http://dx.doi.org/10.1021/jacs.6b01458.
dc.identifier.urihttps://hdl.handle.net/1911/94871
dc.description.abstract Herein 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.language.iso eng
dc.publisher American Chemical Society
dc.rights This is an author's peer-reviewed final manuscript, as accepted by the publisher. The published article is copyrighted by the American Chemical Society.
dc.title Symmetry in Cascade Chirality-Transfer Processes: A Catalytic Atroposelective Direct Arylation Approach to BINOL Derivatives
dc.type Journal article
dc.citation.journalTitle Journal of the American Chemical Society
dc.citation.volumeNumber 138
dc.citation.issueNumber 16
dc.type.dcmi Text
dc.identifier.doihttp://dx.doi.org/10.1021/jacs.6b01458
dc.identifier.pmcid PMC5360188
dc.identifier.pmid 27052566
dc.type.publication post-print
dc.citation.firstpage 5202
dc.citation.lastpage 5205


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