Oxaziridine‐Mediated Oxyamination of Indoles: An Approach to 3‐Aminoindoles and Enantiomerically Enriched 3‐Aminopyrroloindolines
2010; Wiley; Volume: 122; Issue: 48 Linguagem: Inglês
10.1002/ange.201004635
ISSN1521-3757
AutoresTamas Benkovics, Ilia A. Guzei, Tehshik P. Yoon,
Tópico(s)Catalytic C–H Functionalization Methods
ResumoAngewandte ChemieVolume 122, Issue 48 p. 9339-9343 Zuschrift Oxaziridine-Mediated Oxyamination of Indoles: An Approach to 3-Aminoindoles and Enantiomerically Enriched 3-Aminopyrroloindolines† Tamas Benkovics, Tamas Benkovics Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 (USA), Fax: (+1) 608-265-4534 http://yoon.chem.wisc.eduSearch for more papers by this authorDr. Ilia A. Guzei, Dr. Ilia A. Guzei Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 (USA), Fax: (+1) 608-265-4534 http://yoon.chem.wisc.eduSearch for more papers by this authorProf. Tehshik P. Yoon, Corresponding Author Prof. Tehshik P. Yoon [email protected] Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 (USA), Fax: (+1) 608-265-4534 http://yoon.chem.wisc.eduDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 (USA), Fax: (+1) 608-265-4534 http://yoon.chem.wisc.eduSearch for more papers by this author Tamas Benkovics, Tamas Benkovics Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 (USA), Fax: (+1) 608-265-4534 http://yoon.chem.wisc.eduSearch for more papers by this authorDr. Ilia A. Guzei, Dr. Ilia A. Guzei Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 (USA), Fax: (+1) 608-265-4534 http://yoon.chem.wisc.eduSearch for more papers by this authorProf. Tehshik P. Yoon, Corresponding Author Prof. Tehshik P. Yoon [email protected] Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 (USA), Fax: (+1) 608-265-4534 http://yoon.chem.wisc.eduDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 (USA), Fax: (+1) 608-265-4534 http://yoon.chem.wisc.eduSearch for more papers by this author First published: 21 October 2010 https://doi.org/10.1002/ange.201004635Citations: 28 † We thank Kevin Williamson for obtaining X-ray quality crystals of 8, Lara Spencer for determining crystal structures, and Dr. Prakash Raman for insightful discussions. Financial support was provided by the NSF (CHE-0645447) and NIH (GM084022). The NMR spectroscopy facility at UW-Madison is funded by the NIH (S10 RR04981-01) and NSF (CHE-9629688). 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 Das Kerngeschäft im Blick: Eine hoch regioselektive Kupfer(II)-katalysierte Oxyaminierung von N-Acylindolen mit Oxaziridinen führte zu Aminalen, die in einem einzigen Schritt in 3-Aminoindole und 3-Aminopyrroloindoline umgewandelt wurden (siehe Schema). Mit einer chiralen N-Acyl-Gruppe konnte die Kernstruktur einiger faszinierender Pyrroloindolin-Alkaloide mit 91 % ee aufgebaut werden Bs=Benzolsulfonyl, Moc=Methoxycarbonyl. 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 ange_201004635_sm_miscellaneous_information.pdf965.4 KB 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 recent reviews, see: Google Scholar 1aA. Steven, L. E. Overman, Angew. Chem. 2007, 119, 5584–5605; 10.1002/ange.200700612 Google ScholarAngew. Chem. Int. Ed. 2007, 46, 5488–5508; 10.1002/anie.200700612 CASPubMedWeb of Science®Google Scholar 1bJ. Kim, M. Movassaghi, Chem. Soc. Rev. 2009, 38, 3035–3050. 10.1039/b819925f CASPubMedWeb of Science®Google Scholar 2 2aM. Ohno, T. F. Spande, B. Witkop, J. Am. 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