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Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives

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Title: Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives
Authors: Akiyama, Sota Browse this author
Kubota, Koji Browse this author
Mikus, Malte S. Browse this author
Paioti, Paulo H. S. Browse this author
Romiti, Filippo Browse this author
Liu, Qinghe Browse this author
Zhou, Yuebiao Browse this author
Hoveyda, Amir H. Browse this author
Ito, Hajime Browse this author →KAKEN DB
Keywords: boron
enantioselective catalysis
synthetic methods
Issue Date: 13-Jun-2020
Publisher: Wiley-Blackwell
Journal Title: Angewandte chemie-international edition
Volume: 58
Issue: 35
Start Page: 11998
End Page: 12003
Publisher DOI: 10.1002/anie.201906283
Abstract: The first catalytic method for diastereo- and enantioselective synthesis of allylic boronates bearing a Z-trisubstituted alkenyl fluoride is disclosed. Boryl substitution is performed with either a Z- or E-allyldifluoride and is catalyzed by bisphosphine/Cu complexes, affording products in up to 99 % yield with >98:2 Z/E selectivity and 99:1 enantiomeric ratio. A variety of subsequent modifications are feasible, and notable examples are diastereoselective additions to aldehydes/aldimines to access homoallylic alcohols/amines containing a fluorosubstituted stereogenic quaternary center.
Rights: This is the peer reviewed version of the following article: S. Akiyama, K. Kubota, M. S. Mikus, P. H. S. Paioti, F. Romiti, Q. Liu, Y. Zhou, A. H. Hoveyda, H. Ito, Angew. Chem. Int. Ed. 2019, 58, 11998, 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.
Type: article (author version)
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 伊藤 肇

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