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Targeting Structural and Stereochemical Complexity by Organocascade Catalysis: Construction of Spirocyclic Oxindoles Having Multiple Stereocenters

2009; Wiley; Volume: 121; Issue: 39 Linguagem: Inglês

10.1002/ange.200903192

1521-3757

Giorgio Bencivenni, Li‐Yuan Wu, Andrea Mazzanti, Berardino Giannichi, Fabio Pesciaioli, Mao‐Ping Song, Giuseppe Bartoli, Paolo Melchiorre,

Catalytic C–H Functionalization Methods

Angewandte ChemieVolume 121, Issue 39 p. 7336-7339 Zuschrift Targeting Structural and Stereochemical Complexity by Organocascade Catalysis: Construction of Spirocyclic Oxindoles Having Multiple Stereocenters† Giorgio Bencivenni Dr., Giorgio Bencivenni Dr. Dipartimento di Chimica Organica "A. Mangini", Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy) These authors contributed equally to this work.Search for more papers by this authorLi-Yuan Wu, Li-Yuan Wu Department of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Zhengzhou University, Zhengzhou 450052 (P.R. China) These authors contributed equally to this work.Search for more papers by this authorAndrea Mazzanti Dr., Andrea Mazzanti Dr. Dipartimento di Chimica Organica "A. Mangini", Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy)Search for more papers by this authorBerardino Giannichi, Berardino Giannichi Dipartimento di Chimica Organica "A. Mangini", Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy)Search for more papers by this authorFabio Pesciaioli, Fabio Pesciaioli Dipartimento di Chimica Organica "A. Mangini", Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy)Search for more papers by this authorMao-Ping Song Prof., Mao-Ping Song Prof. Department of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Zhengzhou University, Zhengzhou 450052 (P.R. China)Search for more papers by this authorGiuseppe Bartoli Prof., Giuseppe Bartoli Prof. Dipartimento di Chimica Organica "A. Mangini", Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy)Search for more papers by this authorPaolo Melchiorre Dr., Paolo Melchiorre Dr. p.melchiorre@unibo.it Dipartimento di Chimica Organica "A. Mangini", Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy)Search for more papers by this author Giorgio Bencivenni Dr., Giorgio Bencivenni Dr. Dipartimento di Chimica Organica "A. Mangini", Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy) These authors contributed equally to this work.Search for more papers by this authorLi-Yuan Wu, Li-Yuan Wu Department of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Zhengzhou University, Zhengzhou 450052 (P.R. China) These authors contributed equally to this work.Search for more papers by this authorAndrea Mazzanti Dr., Andrea Mazzanti Dr. Dipartimento di Chimica Organica "A. Mangini", Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy)Search for more papers by this authorBerardino Giannichi, Berardino Giannichi Dipartimento di Chimica Organica "A. Mangini", Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy)Search for more papers by this authorFabio Pesciaioli, Fabio Pesciaioli Dipartimento di Chimica Organica "A. Mangini", Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy)Search for more papers by this authorMao-Ping Song Prof., Mao-Ping Song Prof. Department of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Zhengzhou University, Zhengzhou 450052 (P.R. China)Search for more papers by this authorGiuseppe Bartoli Prof., Giuseppe Bartoli Prof. Dipartimento di Chimica Organica "A. Mangini", Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy)Search for more papers by this authorPaolo Melchiorre Dr., Paolo Melchiorre Dr. p.melchiorre@unibo.it Dipartimento di Chimica Organica "A. Mangini", Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy)Search for more papers by this author First published: 09 September 2009 https://doi.org/10.1002/ange.200903192Citations: 164 † The China Scholarship Council is gratefully acknowledged (grant to L.-Y. Wu). This work was supported by Bologna University and by MIUR National Project "Stereoselezione in Sintesi Organica". P.M. thanks one of the referees of the original submission for invaluable advice. 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 onFacebookTwitterLinkedInRedditWechat Graphical Abstract Nicht so schwierig, wie es aussieht: Der asymmetrische Aufbau komplexer Oxindol-Spirocyclen mit mehreren Stereozentren gelang durch Reaktionskaskaden mit zwei Organokatalysatoren, die jeweils unterschiedliche Carbonylverbindungen aktivieren (siehe Schema; TMS=Trimethylsilyl). Die sich ergänzenden Ansätze belegen das Potenzial organokatalytischer Kaskaden für knifflige Syntheseprobleme. 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 ange_200903192_sm_miscellaneous_information.pdf2.6 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. Volume121, Issue39September 14, 2009Pages 7336-7339 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. RelatedInformation