Metal‐Catalyzed Regiodivergent Cyclization of γ‐Allenols: Tetrahydrofurans versus Oxepanes
2007; Wiley; Volume: 46; Issue: 35 Linguagem: Inglês
10.1002/anie.200701611
ISSN1521-3773
AutoresBenito Alcaide, Pedro Almendros, Teresa Martínez del Campo,
Tópico(s)Catalytic C–H Functionalization Methods
ResumoAngewandte Chemie International EditionVolume 46, Issue 35 p. 6684-6687 Communication Metal-Catalyzed Regiodivergent Cyclization of γ-Allenols: Tetrahydrofurans versus Oxepanes† Benito Alcaide Prof. Dr., Benito Alcaide Prof. Dr. [email protected] Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid, Spain, Fax: (+34) 91-394-4103Search for more papers by this authorPedro Almendros Dr., Pedro Almendros Dr. [email protected] Instituto de Química Orgánica General, Consejo Superior de Investigaciones Científicas (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain, Fax: (+34) 91-564-4853Search for more papers by this authorTeresa Martínez del Campo Dipl.-Chem., Teresa Martínez del Campo Dipl.-Chem. Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid, Spain, Fax: (+34) 91-394-4103Search for more papers by this author Benito Alcaide Prof. Dr., Benito Alcaide Prof. Dr. [email protected] Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid, Spain, Fax: (+34) 91-394-4103Search for more papers by this authorPedro Almendros Dr., Pedro Almendros Dr. [email protected] Instituto de Química Orgánica General, Consejo Superior de Investigaciones Científicas (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain, Fax: (+34) 91-564-4853Search for more papers by this authorTeresa Martínez del Campo Dipl.-Chem., Teresa Martínez del Campo Dipl.-Chem. Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid, Spain, Fax: (+34) 91-394-4103Search for more papers by this author First published: 28 August 2007 https://doi.org/10.1002/anie.200701611Citations: 112 † Support for this work by the DGI-MCYT (Project CTQ2006-10292) is gratefully acknowledged. T.M.C. thanks the MEC for a predoctoral grant. 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 Ringing the changes: The 5-exo-trig cyclization pathway of γ-allenols can be completely reversed by either changing the metal (Pd instead of Au) or using a (methoxymethyl)oxy protecting group. As a result, the 7-endo-trig alkoxycyclization dominates instead (see scheme; MOM=MeOCH2; Z1=tBuMe2Si, ArCO). Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2007/z701611_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. Volume46, Issue35September 3, 2007Pages 6684-6687 RelatedInformation
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