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dc.contributor.authorMei, Guang-Jian
dc.contributor.authorZheng, Wenrui
dc.contributor.authorGoncalves, Theo
dc.contributor.authorTang, Xiwen
dc.contributor.authorHuang, Kuo-Wei
dc.contributor.authorLu, Yixin
dc.date.accessioned2020-02-20T06:39:02Z
dc.date.available2020-02-20T06:39:02Z
dc.date.issued2020-01-31
dc.date.submitted2019-12-30
dc.identifier.citationMei, G.-J., Zheng, W., Gonçalves, T. P., Tang, X., Huang, K.-W., & Lu, Y. (2020). Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles. iScience, 100873. doi:10.1016/j.isci.2020.100873
dc.identifier.doi10.1016/j.isci.2020.100873
dc.identifier.urihttp://hdl.handle.net/10754/661577
dc.description.abstractChiral phosphoric acid-catalyzed highly enantioselective formal [3 + 2] cycloaddition reaction of azoalkenes with 3-vinylindoles has been established. Under mild conditions, the projected cycloaddition proceeded smoothly, affording a variety of 2,3-dihydropyrroles in high yields and excellent enantioselectivities, and also in a diastereospecific manner. As opposed to the common 4-atom synthons in the previous literature reports, azoalkenes served as 3-atom synthons. Besides, the observed selectivity was supported by primary theoretical calculation. The unique chemistry of azoalkenes disclosed herein will empower asymmetric synthesis of nitrogen-containing ring structural motifs in a broader context.
dc.description.sponsorshipY.L. thanks the Singapore National Research Foundation, Prime Minister’s Office for the NRF Investigatorship Award (R-143-000-A15-281). Financial supports from the National University of Singapore (R-143-000-695-114 & C-141-000-092-001) and the National Natural Science Foundation of China (21672158 & 21702077) are also gratefully acknowledged.
dc.publisherElsevier BV
dc.relation.urlhttps://linkinghub.elsevier.com/retrieve/pii/S2589004220300572
dc.relation.urlhttp://www.cell.com/article/S2589004220300572/pdf
dc.rightsNOTICE: this is the author’s version of a work that was accepted for publication in iScience. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in iScience, [[Volume], [Issue], (2020-02-17)] DOI: 10.1016/j.isci.2020.100873 . © 2020. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
dc.titleCatalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles.
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentHomogeneous Catalysis Laboratory (HCL)
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journaliScience
dc.eprint.versionPublisher's Version/PDF
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore
dc.contributor.institutionJoint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou, Fujian 359297, PR China
dc.contributor.institutionNational University of Singapore (Suzhou) Research Institute, 377 Lin Quan Street, Suzhou Industrial Park, Suzhou, 215123, China.
kaust.personGoncalves, Theo
kaust.personHuang, Kuo-Wei
dc.date.accepted2020-01-27
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc23pkq3
refterms.dateFOA2020-02-20T06:41:19Z
display.relations<b>Is Supplemented By:</b><br/> <ul><li><i>[Dataset]</i> <br/> Mei, Guang-Jian, Zheng, Wenrui, Gonçalves, Théo P., Tang, Xiwen, Huang, Kuo-Wei, &amp; Lu, Yixin. (2020). <i>CCDC 1957145: Experimental Crystal Structure Determination</i> [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC23PKQ3. DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc23pkq3" >10.5517/ccdc.csd.cc23pkq3</a> Handle: <a href="http://hdl.handle.net/10754/664854" >10754/664854</a></a></li></ul>
dc.date.published-online2020-01-31
dc.date.published-print2020-02


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