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N‐Heterocyclic Carbene Catalyzed CC Bond Cleavage in Redox Esterifications of Chiral Formylcyclopropanes

2006; Wiley; Volume: 118; Issue: 36 Linguagem: Inglês

10.1002/ange.200601919

1521-3757

Stephanie S. Sohn, Jeffrey W. Bode,

N-Heterocyclic Carbenes in Organic and Inorganic Chemistry

Angewandte ChemieVolume 118, Issue 36 p. 6167-6170 Zuschrift N-Heterocyclic Carbene Catalyzed CC Bond Cleavage in Redox Esterifications of Chiral Formylcyclopropanes† Stephanie S. Sohn, Stephanie S. Sohn Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA, USA, Fax: (+1) 805-893-4120 http://www.chem.ucsb.edu/∼bodegroup/Search for more papers by this authorJeffrey W. Bode Prof. Dr., Jeffrey W. Bode Prof. Dr. bode@chem.ucsb.edu Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA, USA, Fax: (+1) 805-893-4120 http://www.chem.ucsb.edu/∼bodegroup/Search for more papers by this author Stephanie S. Sohn, Stephanie S. Sohn Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA, USA, Fax: (+1) 805-893-4120 http://www.chem.ucsb.edu/∼bodegroup/Search for more papers by this authorJeffrey W. Bode Prof. Dr., Jeffrey W. Bode Prof. Dr. bode@chem.ucsb.edu Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA, USA, Fax: (+1) 805-893-4120 http://www.chem.ucsb.edu/∼bodegroup/Search for more papers by this author First published: 05 September 2006 https://doi.org/10.1002/ange.200601919Citations: 44 † This study was supported by the National Science Foundation (CHE-0449587) and the California Cancer Research Coordinating Committee. J.W.B. is grateful to Amgen and Richard and Leslie Anderson for additional support. We are grateful to Sean Riznikove, John Unger, and Bruce Lipshutz (UCSB) for assistance with the chiral GC analyses. 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 Ein sauberer Schnitt: Ein N-heterocyclisches Carben katalysiert die Ringöffnung chiraler nichtracemischer Formylcyclopropane unter gleichzeitiger Oxidation der Aldehydfunktion und ohne Bedarf an stöchiometrischen Reagentien. Das aktivierte Carboxylatintermediat lässt sich mit Nucleophilen abfangen, was zu chiralen Estern, Thioestern oder Carbonsäuren führt (siehe Schema). DBU=1,8-Diazabicyclo[5.4.0]undec-7-en, EWG=elektronenziehende Gruppe. Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2001/2006/z601919_s.pdf or from the author. 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. Volume118, Issue36September 11, 2006Pages 6167-6170 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