Base-Catalyzed Condensation of 2-Hydroxybenzaldehydes with α,β-Unsaturated Aldehydes - Scope and Limitations

Advanced Synthesis & CatalysisVolume 347, Issue 4 p. 555-562 Full Paper Base-Catalyzed Condensation of 2-Hydroxybenzaldehydes with α,β-Unsaturated Aldehydes – Scope and Limitations Bernhard Lesch, Bernhard Lesch Institut für Organische Chemie, Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn, GermanySearch for more papers by this authorJakob Toräng, Jakob Toräng Institut für Organische Chemie, Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn, GermanySearch for more papers by this authorSylvia Vanderheiden, Sylvia Vanderheiden Institut für Organische Chemie, Universität Karlsruhe (TH), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany, Fax: (+49)-721-608-8581Search for more papers by this authorStefan Bräse, Stefan Bräse [email protected] Institut für Organische Chemie, Universität Karlsruhe (TH), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany, Fax: (+49)-721-608-8581Search for more papers by this author Bernhard Lesch, Bernhard Lesch Institut für Organische Chemie, Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn, GermanySearch for more papers by this authorJakob Toräng, Jakob Toräng Institut für Organische Chemie, Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn, GermanySearch for more papers by this authorSylvia Vanderheiden, Sylvia Vanderheiden Institut für Organische Chemie, Universität Karlsruhe (TH), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany, Fax: (+49)-721-608-8581Search for more papers by this authorStefan Bräse, Stefan Bräse [email protected] Institut für Organische Chemie, Universität Karlsruhe (TH), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany, Fax: (+49)-721-608-8581Search for more papers by this author First published: 28 February 2005 https://doi.org/10.1002/adsc.200404239Citations: 62AboutPDF 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 Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract The base-catalyzed condensation of α,β-unsaturated carbonyl compounds with 2-hydroxybenzaldehydes yielding tetrahydroxanthones and dihydrobenzopyrans has been investigated. A novel access to highly functionalized dihydrobenzopyrans via a mild generation of the dienol of senecialdehyde and subsequent conjugated aldol reaction has been reported. Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2258/2005/f4239_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. References 1 Cordiachromene: 1a G. D. Manners, L. Jurd, J. Chem. Soc. Perkin Trans. 1 1977, 405–410; 1b A. F. Benslimane, Y. F. Pouchus, J.-F. 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