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Single-Step Synthesis of Atropisomers with Vicinal C−C and C−N Diaxes by Cobalt-Catalyzed Atroposelective C−H Annulation
dc.contributor.authorWang, Bing-Jie
dc.contributor.authorXu, Guo-Xiong
dc.contributor.authorHuang, Zong-Wei
dc.contributor.authorWu, Xu
dc.contributor.authorHong, Xin
dc.contributor.authorYao, Qi-Jun
dc.contributor.authorShi, Bing-Feng
dc.date.accessioned2022-10-05T15:51:23Z
dc.date.available2023-10-05 11:51:19en
dc.date.available2022-10-05T15:51:23Z
dc.date.issued2022-09-26
dc.identifier.citationWang, Bing-Jie ; Xu, Guo-Xiong ; Huang, Zong-Wei ; Wu, Xu; Hong, Xin; Yao, Qi-Jun ; Shi, Bing-Feng (2022). "Single- Step Synthesis of Atropisomers with Vicinal C- C and C- N Diaxes by Cobalt- Catalyzed Atroposelective C- H Annulation." Angewandte Chemie International Edition 61(39): n/a-n/a.
dc.identifier.issn1433-7851
dc.identifier.issn1521-3773
dc.identifier.urihttps://hdl.handle.net/2027.42/174912
dc.description.abstractThe atroposelective synthesis of atropisomers with vicinal diaxes remains rare and challenging, due to the steric influence between the two axes and their unique topology. Herein, we disclose a single-step construction of atropisomers with vicinal C−C and C−N chiral diaxes by cyclopentadiene (Cp)-free cobalt-catalyzed intramolecular atroposelective C−H annulation, providing the desired diaxial atropisomers of unique structures with decent stereocontrols of both axes (up to >99 % ee and 70 : 1 dr). The optically pure products bearing fluorophores show circular polarized luminescence (CPL) properties, being candidate materials for potential CPL applications. Atropisomerization experiments and density function theory (DFT) calculations are conducted to study the rotational barriers and rotation pathways of the diaxes.A single-step construction of atropisomers with vicinal C−C and C−N chiral diaxes by cyclopentadiene (Cp)-free cobalt-catalyzed intramolecular atroposelective C−H annulation with decent stereocontrols (up to >99 % ee and 70/1 dr) was reported. Atropisomerization experiments and DFT calculations are done to study the rotational barriers and pathways of the diaxes.
dc.publisherWiley Periodicals, Inc.
dc.subject.otherAtroposelectivity
dc.subject.otherC−H Annulation
dc.subject.otherCobalt
dc.subject.otherSalicyloxazoline
dc.subject.otherVicinal Diaxis
dc.titleSingle-Step Synthesis of Atropisomers with Vicinal C−C and C−N Diaxes by Cobalt-Catalyzed Atroposelective C−H Annulation
dc.typeArticle
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/174912/1/anie202208912-sup-0001-misc_information.pdf
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/174912/2/anie202208912_am.pdf
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/174912/3/anie202208912.pdf
dc.identifier.doi10.1002/anie.202208912
dc.identifier.sourceAngewandte Chemie International Edition
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dc.working.doiNOen
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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