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Nickel‐Catalyzed Regio‐ and Stereoselective Reductive Coupling between Methylenecyclopropanes, Aldehydes, and Triethylborane with Retention of the Cyclopropane Ring

2012; Wiley; Volume: 18; Issue: 20 Linguagem: Inglês

10.1002/chem.201200271

1521-3765

Kenichi Ogata, Daisuke Shimada, Shin‐ichi Fukuzawa,

Catalytic Alkyne Reactions

Chemistry – A European JournalVolume 18, Issue 20 p. 6142-6146 Communication Nickel-Catalyzed Regio- and Stereoselective Reductive Coupling between Methylenecyclopropanes, Aldehydes, and Triethylborane with Retention of the Cyclopropane Ring Dr. Kenichi Ogata, Corresponding Author Dr. Kenichi Ogata [email protected] Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551 (Japan), Fax: (+81) 3-3817-1916Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551 (Japan), Fax: (+81) 3-3817-1916Search for more papers by this authorDaisuke Shimada, Daisuke Shimada Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551 (Japan), Fax: (+81) 3-3817-1916Search for more papers by this authorProf. Dr. Shin-ichi Fukuzawa, Corresponding Author Prof. Dr. Shin-ichi Fukuzawa Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551 (Japan), Fax: (+81) 3-3817-1916Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551 (Japan), Fax: (+81) 3-3817-1916Search for more papers by this author Dr. Kenichi Ogata, Corresponding Author Dr. Kenichi Ogata [email protected] Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551 (Japan), Fax: (+81) 3-3817-1916Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551 (Japan), Fax: (+81) 3-3817-1916Search for more papers by this authorDaisuke Shimada, Daisuke Shimada Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551 (Japan), Fax: (+81) 3-3817-1916Search for more papers by this authorProf. Dr. Shin-ichi Fukuzawa, Corresponding Author Prof. Dr. Shin-ichi Fukuzawa Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551 (Japan), Fax: (+81) 3-3817-1916Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551 (Japan), Fax: (+81) 3-3817-1916Search for more papers by this author First published: 16 April 2012 https://doi.org/10.1002/chem.201200271Citations: 15Read 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 Running rings: The first regio- and stereoselective reductive coupling between methylenecyclopropanes, aldehydes, and triethylborane with retention of the cyclopropane ring was achieved using a nickel–phosphine catalyst (see scheme). The reductive coupling reaction constructed a stereo-defined cyclopropane ring with formation of a quaternary stereogenic carbon center. 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 chem_201200271_sm_miscellaneous_information.pdf5.3 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. Volume18, Issue20May 14, 2012Pages 6142-6146 RelatedInformation