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 |
copper |
enantioselective catalysis |
fluorine |
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 https://doi.org/10.1002/anie.201906283. 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) |
URI: | http://hdl.handle.net/2115/79109 |
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)
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