Nickel‐Catalyzed Cycloaddition of α,β,γ,δ‐Unsaturated Ketones with Alkynes

Angewandte Chemie International EditionVolume 50, Issue 38 p. 8956-8959 Communication Nickel-Catalyzed Cycloaddition of α,β,γ,δ-Unsaturated Ketones with Alkynes† Hiroaki Horie, Hiroaki Horie Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510 (Japan)Search for more papers by this authorDr. Takuya Kurahashi, Corresponding Author Dr. Takuya Kurahashi tkuraha@orgrxn.mbox.media.kyoto-u.ac.jp Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510 (Japan)Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510 (Japan)Search for more papers by this authorProf. Dr. Seijiro Matsubara, Corresponding Author Prof. Dr. Seijiro Matsubara matsubar@orgrxn.mbox.media.kyoto-u.ac.jp Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510 (Japan)Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510 (Japan)Search for more papers by this author Hiroaki Horie, Hiroaki Horie Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510 (Japan)Search for more papers by this authorDr. Takuya Kurahashi, Corresponding Author Dr. Takuya Kurahashi tkuraha@orgrxn.mbox.media.kyoto-u.ac.jp Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510 (Japan)Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510 (Japan)Search for more papers by this authorProf. Dr. Seijiro Matsubara, Corresponding Author Prof. Dr. Seijiro Matsubara matsubar@orgrxn.mbox.media.kyoto-u.ac.jp Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510 (Japan)Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510 (Japan)Search for more papers by this author First published: 19 August 2011 https://doi.org/10.1002/anie.201104286Citations: 13 † This study was supported by Grants-in-Aid from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) (Japan). T.K. also acknowledges the support of the Asahi Glass Foundation, Kansai Research Foundation, and Toyota Physical and Chemical Research Institute. 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 As easy as α, β, γ, δ: The title reaction unexpectedly resulted in the stereoselective synthesis of bicyclo[3.1.0]hexenes (see scheme). The high level of stereoselection is attributed to a mechanistic pathway involving the oxidative cyclization of nickel(0) with α,β,γ,δ-unsaturated ketones and alkynes, and the subsequent intramolecular carbonickelation. 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_201104286_sm_miscellaneous_information.pdf6.6 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, Issue38September 12, 2011Pages 8956-8959 RelatedInformation