Show simple item record

dc.contributor.authorZhao, Changgui
dc.contributor.authorGuo, Donghui
dc.contributor.authorMunkerup, Kristin
dc.contributor.authorHuang, Kuo-Wei
dc.contributor.authorLi, Fangyi
dc.contributor.authorWang, Jian
dc.date.accessioned2018-02-13T13:43:18Z
dc.date.available2018-02-13T13:43:18Z
dc.date.issued2018-02-09
dc.identifier.citationZhao C, Guo D, Munkerup K, Huang K-W, Li F, et al. (2018) Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes. Nature Communications 9. Available: http://dx.doi.org/10.1038/s41467-018-02952-3.
dc.identifier.issn2041-1723
dc.identifier.pmid29426851
dc.identifier.doi10.1038/s41467-018-02952-3
dc.identifier.urihttp://hdl.handle.net/10754/627116
dc.description.abstractAxially chiral molecules are among the most valuable substrates in organic synthesis. They are typically used as chiral ligands or catalysts in asymmetric reactions. Recent progress for the construction of these chiral molecules is mainly focused on the transition-metal-catalyzed transformations. Here, we report the enantioselective NHC-catalyzed (NHC: N-heterocyclic carbenes) atroposelective annulation of cyclic 1,3-diones with ynals. In the presence of NHC precatalyst, base, Lewis acid and oxidant, a catalytic C–C bond formation occurs, providing axially chiral α-pyrone−aryls in moderate to good yields and with high enantioselectivities. Control experiments indicated that alkynyl acyl azoliums, acting as active intermediates, are employed to atroposelectively assemble chiral biaryls and such a methodology may be creatively applied to other useful NHC-catalyzed asymmetric transformations.
dc.description.sponsorshipGenerous financial supports for this work were provided by: the National Natural Science Foundation of China (21672121), the “Thousand Plan” Youth program of China, the Tsinghua University, the Bayer Investigator fellow, the fellowship of Tsinghua-Peking centre for life sciences (CLS), and the China Postdoctoral Science Foundation (2015M570072) to J.W., and KAUST to K.-W.H.
dc.publisherSpringer Nature
dc.relation.urlhttps://www.nature.com/articles/s41467-018-02952-3
dc.rightsThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.titleEnantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes
dc.typeArticle
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Division
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.journalNature Communications
dc.eprint.versionPublisher's Version/PDF
dc.contributor.institutionSchool of Pharmaceutical Sciences, Collaborative Innovation Center for Diagnosis and Treatment of Infectious Diseases, Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology (Ministry of Education), Tsinghua University Beijing, 100084, Beijing, China
kaust.personMunkerup, Kristin
kaust.personHuang, Kuo-Wei
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc1mcymk
refterms.dateFOA2018-06-14T05:16:39Z
display.relations<b>Is Supplemented By:</b><br/> <ul><li><i>[Dataset]</i> <br/> Zhao, C., Guo, D., Munkerup, K., Huang, K.-W., Li, F., &amp; Wang, J. (2018). <i>CCDC 1501039: Experimental Crystal Structure Determination</i> [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC1MCYMK. DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc1mcymk" >10.5517/ccdc.csd.cc1mcymk</a> Handle: <a href="http://hdl.handle.net/10754/664018" >10754/664018</a></a></li></ul>
dc.date.published-online2018-02-09
dc.date.published-print2018-12


Files in this item

Thumbnail
Name:
s41467-018-02952-3.pdf
Size:
1.156Mb
Format:
PDF
Description:
Published version
Thumbnail
Name:
41467_2018_2952_MOESM1_ESM.pdf
Size:
4.728Mb
Format:
PDF
Description:
Supplemental files
Thumbnail
Name:
41467_2018_2952_MOESM2_ESM.pdf
Size:
778.2Kb
Format:
PDF
Description:
Supplemental files

This item appears in the following Collection(s)

Show simple item record

This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
Except where otherwise noted, this item's license is described as This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.