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Rhodium(I)-Catalyzed Enantioselective Cyclization of Enynes through Site-Selective C(sp3)-H Bond Activation Triggered by Formation of Rhodacycle
| Title: | Rhodium(I)-Catalyzed Enantioselective Cyclization of Enynes through Site-Selective C(sp3)-H Bond Activation Triggered by Formation of Rhodacycle |
| Authors: | Oonishi, Yoshihiro Browse this author →KAKEN DB | | Sakamoto, Shunki Browse this author | | Agata, Shuya Browse this author | | Sato, Yoshihiro Browse this author →KAKEN DB |
| Keywords: | rhodium | | enantioselective cyclization | | C(sp3)-H bond activation | | alkene | | alkyne | | enyne |
| Issue Date: | 30-Mar-2021 |
| Publisher: | Georg Thieme Verlag |
| Journal Title: | Synthesis |
| Volume: | 53 |
| Issue: | 17 |
| Start Page: | 2976 |
| End Page: | 2983 |
| Publisher DOI: | 10.1055/a-1469-7408 |
| Abstract: | Rhodium(I)-catalyzed enantioselective cyclization of enynes through C(sp3)-H bond activation was investigated. It was found that the cyclization of enynes having a tert-butyl moiety on the alkene afforded a spirocyclic compound (up to 92% ee), while the cyclization of enynes having an isopropyl or an ethyl group on the alkene gave a cyclic diene (up to 98% ee). Furthermore, an intermolecular competition reaction using a deuterium-labeled substrate revealed that C(sp3)-H bond activation was one of the key steps, having a high energy barrier, in this cyclization. |
| Rights: | This is an Accepted Manuscript of an article published by Thieme Publishing Group in Journal Title on Publication Date, available online at https://www.thieme-connect.de/products/ejournals/abstract/10.1055/a-1469-7408 |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/84694 |
| Appears in Collections: | 薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 大西 英博
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