| 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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