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Cu(I)-Catalyzed Enantioselective gamma-Boryl Substitution of Trifluoromethyl- and Silyl-Substituted Alkenes

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Title: Cu(I)-Catalyzed Enantioselective gamma-Boryl Substitution of Trifluoromethyl- and Silyl-Substituted Alkenes
Authors: Oyama, Natsuki Browse this author
Akiyama, Sota Browse this author
Kubota, Koji Browse this author
Imamoto, Tsuneo Browse this author
Ito, Hajime Browse this author →KAKEN DB
Keywords: Borylation
Issue Date: 19-Aug-2022
Publisher: Wiley-Blackwell
Journal Title: European journal of organic chemistry
Volume: 2022
Issue: 31
Start Page: e202200664
Publisher DOI: 10.1002/ejoc.202200664
Abstract: Asymmetric gamma-boryl substitution of trifluoromethyl- and silyl-substituted alkenes has been investigated. A variety of substrates were reacted with bis(pinacolato)diboron in the presence of a copper(I) salt and optically active C-1 symmetric QuinoxP*-type bisphosphine ligand as the catalyst. The optically active silyl-substituted gem-difluoroallylboronates products bearing a stereogenic C-B bond, which have never been synthesized before, were obtained in good yield with high enantioselectivity (up to 83% and up to 86% ee, respectively). The resulting allylboron compounds undergo a stereoselective allylboration with a range of aldehydes to afford chiral silyl- and difluoromethylene-containing homoallylic alcohols without significant loss in their enantiomeric purity. The resulting silyl groups in the derivatives can serve as cross-coupling sites, allowing further transformation into structurally complex fluorinated chiral molecules.
Rights: This is the peer reviewed version of the following article: N. Oyama, S. Akiyama, K. Kubota, T. Imamoto, H. Ito, Eur. J. Org. Chem. 2022, e202200664, which has been published in final form at This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.
Type: article (author version)
Appears in Collections:総合化学院 (Graduate School of Chemical Sciences and Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 大山 夏生

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