Nickel‐Catalyzed Enantioselective Arylation of Pyridinium Ions: Harnessing an Iminium Ion Activation Mode
2013; Wiley; Volume: 125; Issue: 35 Linguagem: Inglês
10.1002/ange.201303994
ISSN1521-3757
AutoresStephen T. Chau, J. Patrick Lutz, Kevin Wu, Abigail G. Doyle,
Tópico(s)Asymmetric Hydrogenation and Catalysis
ResumoAngewandte ChemieVolume 125, Issue 35 p. 9323-9326 Zuschrift Nickel-Catalyzed Enantioselective Arylation of Pyridinium Ions: Harnessing an Iminium Ion Activation Mode† Stephen T. Chau, Stephen T. Chau Department of Chemistry, Princeton University, Washington Rd, Princeton, NJ 08544-1009 (USA) http://www.princeton.edu/∼doylegrp/Search for more papers by this authorJ. Patrick Lutz, J. Patrick Lutz Department of Chemistry, Princeton University, Washington Rd, Princeton, NJ 08544-1009 (USA) http://www.princeton.edu/∼doylegrp/Search for more papers by this authorKevin Wu, Kevin Wu Department of Chemistry, Princeton University, Washington Rd, Princeton, NJ 08544-1009 (USA) http://www.princeton.edu/∼doylegrp/Search for more papers by this authorProf. Abigail G. Doyle, Corresponding Author Prof. Abigail G. Doyle [email protected] Department of Chemistry, Princeton University, Washington Rd, Princeton, NJ 08544-1009 (USA) http://www.princeton.edu/∼doylegrp/Department of Chemistry, Princeton University, Washington Rd, Princeton, NJ 08544-1009 (USA) http://www.princeton.edu/∼doylegrp/Search for more papers by this author Stephen T. Chau, Stephen T. Chau Department of Chemistry, Princeton University, Washington Rd, Princeton, NJ 08544-1009 (USA) http://www.princeton.edu/∼doylegrp/Search for more papers by this authorJ. Patrick Lutz, J. Patrick Lutz Department of Chemistry, Princeton University, Washington Rd, Princeton, NJ 08544-1009 (USA) http://www.princeton.edu/∼doylegrp/Search for more papers by this authorKevin Wu, Kevin Wu Department of Chemistry, Princeton University, Washington Rd, Princeton, NJ 08544-1009 (USA) http://www.princeton.edu/∼doylegrp/Search for more papers by this authorProf. Abigail G. Doyle, Corresponding Author Prof. Abigail G. Doyle [email protected] Department of Chemistry, Princeton University, Washington Rd, Princeton, NJ 08544-1009 (USA) http://www.princeton.edu/∼doylegrp/Department of Chemistry, Princeton University, Washington Rd, Princeton, NJ 08544-1009 (USA) http://www.princeton.edu/∼doylegrp/Search for more papers by this author First published: 10 July 2013 https://doi.org/10.1002/ange.201303994Citations: 20 † We thank Phil Jeffrey for X-ray crystallographic structure determination of 2 b and 3. Financial support provided by Princeton University and Boehringer Ingelheim is gratefully acknowledged. A.G.D. is an Alfred P. Sloan Foundation Fellow, an Eli Lilly Grantee, an Amgen Young Investigator, and a Roche Early Excellence in Chemistry Awardee. Read the full textAboutPDF ToolsRequest permissionAdd to favorites 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 Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Die enantioselektive Kreuzkupplung zwischen N-Acylpyridinium-Salzen und Organozinkreagentien nutzt ein Katalysatorsystem aus einer luftbeständigen Nickel(II)-Quelle und einem chiralen Phosphoramiditliganden für die Synthese von 2-substituierten 2,3-Dihydro-4-pyridonen mit bis >99 % ee. Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Filename Description ange_201303994_sm_miscellaneous_information.pdf8.4 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. References 1For a review, see: Google Scholar 1aM. Beller, M. Eckert, Angew. Chem. 2000, 112, 1026–1044; 10.1002/(SICI)1521-3757(20000317)112:6 3.0.CO;2-D Google ScholarAngew. Chem. Int. Ed. 2000, 39, 1010–1027; for selected examples, see: 10.1002/(SICI)1521-3773(20000317)39:6 3.0.CO;2-P CASPubMedWeb of Science®Google Scholar 1bY. Lu, B. A. Arndtsen, Org. 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