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One‐Step Catalytic Asymmetric Synthesis of Configurationally Stable Tröger Bases

2011; Wiley; Volume: 50; Issue: 16 Linguagem: Inglês

10.1002/anie.201100134

1521-3773

Ankit Sharma, Laure Guénée, Jean‐Valère Naubron, Jérôme Lacour,

Traditional and Medicinal Uses of Annonaceae

Angewandte Chemie International EditionVolume 50, Issue 16 p. 3677-3680 Communication One-Step Catalytic Asymmetric Synthesis of Configurationally Stable Tröger Bases† Ankit Sharma, Ankit Sharma Department of Organic Chemistry, University of Geneva quai Ernest Ansermet 30, 1211 Genève 4 (Switzerland), Fax: (+41) 22-379-3215 http://www.unige.ch/sciences/chiorg/lacour/Search for more papers by this authorDr. Laure Guénée, Dr. Laure Guénée Laboratory of Crystallography, University of Geneva quai Ernest Ansermet 24, 1211 Genève 4 (Switzerland)Search for more papers by this authorDr. Jean-Valère Naubron, Dr. Jean-Valère Naubron Spectropole—Campus Saint Jérôme, 13397 Marseille Cedex 20 (France)Search for more papers by this authorProf. Jérôme Lacour, Corresponding Author Prof. Jérôme Lacour [email protected] Department of Organic Chemistry, University of Geneva quai Ernest Ansermet 30, 1211 Genève 4 (Switzerland), Fax: (+41) 22-379-3215 http://www.unige.ch/sciences/chiorg/lacour/Department of Organic Chemistry, University of Geneva quai Ernest Ansermet 30, 1211 Genève 4 (Switzerland), Fax: (+41) 22-379-3215 http://www.unige.ch/sciences/chiorg/lacour/Search for more papers by this author Ankit Sharma, Ankit Sharma Department of Organic Chemistry, University of Geneva quai Ernest Ansermet 30, 1211 Genève 4 (Switzerland), Fax: (+41) 22-379-3215 http://www.unige.ch/sciences/chiorg/lacour/Search for more papers by this authorDr. Laure Guénée, Dr. Laure Guénée Laboratory of Crystallography, University of Geneva quai Ernest Ansermet 24, 1211 Genève 4 (Switzerland)Search for more papers by this authorDr. Jean-Valère Naubron, Dr. Jean-Valère Naubron Spectropole—Campus Saint Jérôme, 13397 Marseille Cedex 20 (France)Search for more papers by this authorProf. Jérôme Lacour, Corresponding Author Prof. Jérôme Lacour [email protected] Department of Organic Chemistry, University of Geneva quai Ernest Ansermet 30, 1211 Genève 4 (Switzerland), Fax: (+41) 22-379-3215 http://www.unige.ch/sciences/chiorg/lacour/Department of Organic Chemistry, University of Geneva quai Ernest Ansermet 30, 1211 Genève 4 (Switzerland), Fax: (+41) 22-379-3215 http://www.unige.ch/sciences/chiorg/lacour/Search for more papers by this author First published: 18 March 2011 https://doi.org/10.1002/anie.201100134Citations: 61 † We thank Dr. D. Jeannerat and A. Pinto for NMR measurements, the University of Geneva, and the Swiss National Science Foundation for financial support. We also acknowledge the contributions of the Sciences Mass Spectrometry (SMS) platform at the Faculty of Sciences (University of Geneva), and the CRCMM and the Spectropole at the University of Aix-Marseille for computer time and use of the VCD facility, respectively. 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 Bridging the gap: Configurationally stable ethano-bridged Tröger bases have been prepared in a single step by the direct rhodium(II)-catalyzed reaction of methano-bridged Tröger bases and diazo esters (see scheme). The process is general, enantiospecific, diastereoselective (with introduction of a new quaternary carbon center), and regioselective. 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_201100134_sm_miscellaneous_information.pdf2.3 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. Volume50, Issue16April 11, 2011Pages 3677-3680 RelatedInformation