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Rhodium‐Catalyzed Regio‐ and Enantioselective Intermolecular [4+2] Carbocyclization of 4‐Alkynals with N , N ‐Dialkyl Acrylamides

2005; Wiley; Volume: 44; Issue: 44 Linguagem: Inglês

10.1002/anie.200502380

1521-3773

Ken Tanaka, Yuji Hagiwara, Keiichi Noguchi,

Cyclopropane Reaction Mechanisms

Angewandte Chemie International EditionVolume 44, Issue 44 p. 7260-7263 Communication Rhodium-Catalyzed Regio- and Enantioselective Intermolecular [4+2] Carbocyclization of 4-Alkynals with N,N-Dialkyl Acrylamides† Ken Tanaka Prof. Dr., Ken Tanaka Prof. Dr. tanaka-k@cc.tuat.ac.jp Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan, Fax: (+81) 42-388-7037Search for more papers by this authorYuji Hagiwara, Yuji Hagiwara Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan, Fax: (+81) 42-388-7037Search for more papers by this authorKeiichi Noguchi Prof. Dr., Keiichi Noguchi Prof. Dr. Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, JapanSearch for more papers by this author Ken Tanaka Prof. Dr., Ken Tanaka Prof. Dr. tanaka-k@cc.tuat.ac.jp Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan, Fax: (+81) 42-388-7037Search for more papers by this authorYuji Hagiwara, Yuji Hagiwara Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan, Fax: (+81) 42-388-7037Search for more papers by this authorKeiichi Noguchi Prof. Dr., Keiichi Noguchi Prof. Dr. Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, JapanSearch for more papers by this author First published: 08 November 2005 https://doi.org/10.1002/anie.200502380Citations: 53 † We thank Solvias AG for a gift of chiral ligands 5, 6, and 7 under their University Ligand Kit program. We also thank Dr. Masayuki Watanabe (JASCO Corp.) for his circular dichroism exciton chirality analysis and Professor Gregory C. Fu (Massachusetts Institute of Technology) for his helpful encouragement. 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 Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract Selective rings: A cationic RhI–(R,R)-walphos complex catalyzes a highly regio- and enantioselective intermolecular [4+2] carbocyclization of 4-alkynals with N,N-dialkyl acrylamides to afford enantioenriched cyclohexanones (see scheme; cod=cycloocta-1,5-diene). This new route is attractive in view of the one-step access to 4-alkynals from commercially available reagents. Citing Literature Supporting Information Supporting information for this article (full procedures and characterization data) is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z502380_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. Volume44, Issue44November 11, 2005Pages 7260-7263 RelatedInformation