Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes

Handle URI:
http://hdl.handle.net/10754/627116
Title:
Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes
Authors:
Zhao, Changgui; Guo, Donghui; Munkerup, Kristin ( 0000-0001-7097-8133 ) ; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Li, Fangyi; Wang, Jian ( 0000-0003-1884-4546 )
Abstract:
Axially 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.
KAUST Department:
Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC); Biological and Environmental Sciences and Engineering (BESE) Division
Citation:
Zhao 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.
Publisher:
Springer Nature
Journal:
Nature Communications
Issue Date:
5-Feb-2018
DOI:
10.1038/s41467-018-02952-3
Type:
Article
ISSN:
2041-1723
Sponsors:
Generous 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.
Additional Links:
https://www.nature.com/articles/s41467-018-02952-3
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC); Biological and Environmental Sciences and Engineering (BESE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorZhao, Changguien
dc.contributor.authorGuo, Donghuien
dc.contributor.authorMunkerup, Kristinen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorLi, Fangyien
dc.contributor.authorWang, Jianen
dc.date.accessioned2018-02-13T13:43:18Z-
dc.date.available2018-02-13T13:43:18Z-
dc.date.issued2018-02-05en
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.en
dc.identifier.issn2041-1723en
dc.identifier.doi10.1038/s41467-018-02952-3en
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.en
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.en
dc.publisherSpringer Natureen
dc.relation.urlhttps://www.nature.com/articles/s41467-018-02952-3en
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/.en
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/en
dc.titleEnantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenesen
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Divisionen
dc.identifier.journalNature Communicationsen
dc.eprint.versionPublisher's Version/PDFen
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, Chinaen
kaust.authorMunkerup, Kristinen
kaust.authorHuang, Kuo-Weien
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