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Diastereoselective Synthesis of C3‐Quaternary Indolenines Using α,β‐Unsaturated N ‐Aryl Ketonitrones and Activated Alkynes

2012; Wiley; Volume: 51; Issue: 21 Linguagem: Inglês

10.1002/anie.201200860

ISSN

1521-3773

Autores

C. Bryan Huehls, Tyler S. Hood, Jiong Yang,

Tópico(s)

Synthesis and Catalytic Reactions

Resumo

Angewandte Chemie International EditionVolume 51, Issue 21 p. 5110-5113 Communication Diastereoselective Synthesis of C3-Quaternary Indolenines Using α,β-Unsaturated N-Aryl Ketonitrones and Activated Alkynes† Correction(s) for this article Corrigendum: Diastereoselective Synthesis of C3-Quaternary Indolenines Using α,β-Unsaturated N-Aryl Ketonitrones and Activated Alkynes C. Bryan Huehls, Tyler S. Hood, Jiong Yang, Volume 52Issue 49Angewandte Chemie International Edition pages: 12770-12770 First Published online: November 27, 2013 C. Bryan Huehls, C. Bryan Huehls Department of Chemistry, Texas A&M University, College Station, TX 77843-3255 (USA) http://www.chem.tamu.edu/rgroup/yangSearch for more papers by this authorTyler S. Hood, Tyler S. Hood Department of Chemistry, Texas A&M University, College Station, TX 77843-3255 (USA) http://www.chem.tamu.edu/rgroup/yangSearch for more papers by this authorProf. Dr. Jiong Yang, Corresponding Author Prof. Dr. Jiong Yang [email protected] Department of Chemistry, Texas A&M University, College Station, TX 77843-3255 (USA) http://www.chem.tamu.edu/rgroup/yangDepartment of Chemistry, Texas A&M University, College Station, TX 77843-3255 (USA) http://www.chem.tamu.edu/rgroup/yangSearch for more papers by this author C. Bryan Huehls, C. Bryan Huehls Department of Chemistry, Texas A&M University, College Station, TX 77843-3255 (USA) http://www.chem.tamu.edu/rgroup/yangSearch for more papers by this authorTyler S. Hood, Tyler S. Hood Department of Chemistry, Texas A&M University, College Station, TX 77843-3255 (USA) http://www.chem.tamu.edu/rgroup/yangSearch for more papers by this authorProf. Dr. Jiong Yang, Corresponding Author Prof. Dr. Jiong Yang [email protected] Department of Chemistry, Texas A&M University, College Station, TX 77843-3255 (USA) http://www.chem.tamu.edu/rgroup/yangDepartment of Chemistry, Texas A&M University, College Station, TX 77843-3255 (USA) http://www.chem.tamu.edu/rgroup/yangSearch for more papers by this author First published: 05 April 2012 https://doi.org/10.1002/anie.201200860Citations: 30 † We thank Dr. Joseph H. Reibenspies of the X-ray Diffraction Laboratory in the Department of Chemistry at Texas A&M University for X-ray crystallography analysis, Dr. Peddabuddi Gopal of the same department for some preliminary studies, and Professors Kevin Burgess and Daniel Singleton of the same department for helpful discussions. Financial support was provided by Texas A&M University and the Welch Foundation (A-1700). Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Graphical Abstract New trick for an old dog: C3-Quaternary indolenines were synthesized by combining readily available α,β-unsaturated N-aryl ketonitrones and activated alkynes. This remarkably simple and atom-economical transformation does not require transition-metal catalysis and involves the formation of the heterocycles with concomitant generation of two contiguous quaternary and tertiary chiral centers. References 1 1aR. J. 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Soc. 2006, 128, 6330– 6331. 24R. Hoffmann, Chem. Rev. 1989, 89, 1841– 1860. 25CCDC 873391 (2 a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Citing Literature Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_201200860_sm_miscellaneous_information.pdf14.8 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume51, Issue21May 21, 2012Pages 5110-5113 ReferencesRelatedInformation

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