Nickel‐Catalyzed Enantio‐ and Diastereoselective Three‐Component Coupling of 1,3‐Dienes, Aldehydes, and a Silylborane Leading to α‐Chiral Allylsilanes

Angewandte Chemie International EditionVolume 51, Issue 5 p. 1228-1231 Communication Nickel-Catalyzed Enantio- and Diastereoselective Three-Component Coupling of 1,3-Dienes, Aldehydes, and a Silylborane Leading to α-Chiral Allylsilanes† Dr. Nozomi Saito, Corresponding Author Dr. Nozomi Saito [email protected] Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812 (Japan)Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812 (Japan)Search for more papers by this authorAyami Kobayashi, Ayami Kobayashi Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812 (Japan)Search for more papers by this authorProf. Dr. Yoshihiro Sato, Corresponding Author Prof. Dr. Yoshihiro Sato Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812 (Japan)Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812 (Japan)Search for more papers by this author Dr. Nozomi Saito, Corresponding Author Dr. Nozomi Saito [email protected] Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812 (Japan)Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812 (Japan)Search for more papers by this authorAyami Kobayashi, Ayami Kobayashi Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812 (Japan)Search for more papers by this authorProf. Dr. Yoshihiro Sato, Corresponding Author Prof. Dr. Yoshihiro Sato Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812 (Japan)Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812 (Japan)Search for more papers by this author First published: 15 December 2011 https://doi.org/10.1002/anie.201107360Citations: 68 † This work was supported by a Grant-in-Aid for Science Research on Priority Areas (Nos. 19027005 and 20036005, Synergy of Elements) from MEXT (Japan) and a Grant-in-Aid for Scientific Research (B) (No. 23390001) from JSPS. N.S. acknowledges the NOVARTIS Foundation (Japan) for the Promotion of Science and the Takeda Science Foundation for financial support. 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 onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Three-in-one: The nickel-catalyzed asymmetric three-component coupling of 1,3-dienes, aldehydes, and a silylborane in the presence of a chiral phosphoroamidite ligand has been realized. The reaction proceeds by σ-bond metathesis of an oxanickelacycle intermediate with the silylborane to afford the corresponding α-chiral allylsilane derivative in a highly diastereo- and enantioselective manner. 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_201107360_sm_miscellaneous_information.pdf800 KB 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. References 1For reviews on the bismetalation of unsaturated bonds, see: 1aI. Beletskaya, C. Moberg, Chem. Rev. 1999, 99, 3435; 1bL.-B. Han, M. Tanaka, Chem. Commun. 1999, 395; 1cY. Ito, J. Organomet. 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