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Enantioselective Metal‐Free Diamination of Styrenes

2011; Wiley; Volume: 50; Issue: 40 Linguagem: Inglês

10.1002/anie.201103077

ISSN

1521-3773

Autores

Caren Röben, José A. Souto, Y. González, Anton Lishchynskyi, Kilian Muñiz,

Tópico(s)

Catalytic C–H Functionalization Methods

Resumo

Angewandte Chemie International EditionVolume 50, Issue 40 p. 9478-9482 Communication Enantioselective Metal-Free Diamination of Styrenes† Dr. Caren Röben, Dr. Caren Röben Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain) http://www.iciq.es These authors contributed equally to this work.Search for more papers by this authorDr. José A. Souto, Dr. José A. Souto Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain) http://www.iciq.es These authors contributed equally to this work.Search for more papers by this authorYolanda González, Yolanda González Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain) http://www.iciq.esSearch for more papers by this authorAnton Lishchynskyi, Anton Lishchynskyi Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain) http://www.iciq.esSearch for more papers by this authorProf. Dr. Kilian Muñiz, Corresponding Author Prof. Dr. Kilian Muñiz [email protected] Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain) http://www.iciq.es Catalan Institution for Research and Advanced Studies (ICREA), Pg. Lluís Companys 23, 08010 Barcelona (Spain)Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain) http://www.iciq.esSearch for more papers by this author Dr. Caren Röben, Dr. Caren Röben Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain) http://www.iciq.es These authors contributed equally to this work.Search for more papers by this authorDr. José A. Souto, Dr. José A. Souto Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain) http://www.iciq.es These authors contributed equally to this work.Search for more papers by this authorYolanda González, Yolanda González Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain) http://www.iciq.esSearch for more papers by this authorAnton Lishchynskyi, Anton Lishchynskyi Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain) http://www.iciq.esSearch for more papers by this authorProf. Dr. Kilian Muñiz, Corresponding Author Prof. Dr. Kilian Muñiz [email protected] Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain) http://www.iciq.es Catalan Institution for Research and Advanced Studies (ICREA), Pg. Lluís Companys 23, 08010 Barcelona (Spain)Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain) http://www.iciq.esSearch for more papers by this author First published: 30 August 2011 https://doi.org/10.1002/anie.201103077Citations: 257 † We thank Fundación ICIQ, the Consolider INTECAT 2010 (Project CSD2006-0003), the Alexander von Humboldt Foundation (fellowship to C.R.), and the French MESR (fellowship to A.L.) for financial support, and Dr. Á. Iglesias for discussions. 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 Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Metal-free and asymmetric: The first enantioselective diamination of styrenes simply requires a chiral hypervalent iodine(III) reagent as an oxidant and bismesylimide as a nitrogen source (see scheme, Ms=methanesulfonyl). The reaction proceeds under mild conditions and with high enantiomeric excess. 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_201103077_sm_miscellaneous_information.pdf4.1 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. 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Chem. 2006, 71, 8316. 13Further details are included within the Supporting Information. 14CCDC 820374 (2 a), 820375 (7), 827371 (2 g), 827372 (2 u), 827373 (2 o), 827374 (2 p), and 811769 (2 v) 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 . 15Compounds with IIIIN bonds usually lack stability when not stabilized by chelation,[1b] for exceptions, see: 15aI. M. Lazbin, G. F. Koser, J. Org. Chem. 1987, 52, 477; 15bL. Hadjiarapoglou, S. Spyroudis, A. Varvoglis, Synthesis 1983, 207. However, these compounds are unreactive toward alkenes. 16Ligand-exchange reactions on 3, where the acetate group is replaced by a nitrogen-containing group was also proposed for the aziridination reactions, although no definite experimental proof could be obtained.[6a] 17For a detailed study on acid acceleration in diacetoxylation of alkenes: Y.-B. Kang, L. H. Gade, J. Am. Chem. Soc. 2011, 133, 3658. 18After reductive work-up the aryl iodide can be recovered quantitatively and re-oxidized to 5 a.[14] 19 19aG. F. Koser, L. Rebrovic, R. H. Wettach, J. Org. Chem. 1981, 46, 4324; 19bN. S. Zefirov, V. V. Zhdankin, Y. V. Dan’kov, V. D. Sorokin, V. N. Semerikov, A. S. Koz’min, R. Caple, B. A. Berglund, Tetrahedron Lett. 1986, 27, 3971. 20For a related proposal: H. M. Lovick, F. E. Michael, J. Am. Chem. Soc. 2010, 132, 1249. 21F. Bergel, J. Butler, J. Chem. Soc. 1961, 4047. 22A. H. M. Raeymaekers, L. F. C. Roevens, P. A. J. Janssen, Tetrahedron Lett. 1967, 8, 1467. Citing Literature Volume50, Issue40September 26, 2011Pages 9478-9482 ReferencesRelatedInformation

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