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Rhodium(I)-Catalyzed Enantioselective Cyclization of Enynes by Intramolecular Cleavage of the Rh-C Bond by a Tethered Hydroxy Group
| Title: | Rhodium(I)-Catalyzed Enantioselective Cyclization of Enynes by Intramolecular Cleavage of the Rh-C Bond by a Tethered Hydroxy Group |
| Authors: | Oonishi, Yoshihiro Browse this author →KAKEN DB | | Masusaki, Shuichi Browse this author | | Sakamoto, Shunki Browse this author | | Sato, Yoshihiro Browse this author →KAKEN DB |
| Keywords: | cyclization | | enantioselectivity | | enyne | | rhodium | | sigma-bond metathesis |
| Issue Date: | 24-Jun-2019 |
| Publisher: | Wiley-Blackwell |
| Journal Title: | Angewandte chemie-international edition |
| Volume: | 58 |
| Issue: | 26 |
| Start Page: | 8736 |
| End Page: | 8739 |
| Publisher DOI: | 10.1002/anie.201902832 |
| Abstract: | Rhodium(I)-catalyzed enantioselective intramolecular cyclization of enynes having a hydroxy group in the tether was investigated, and various cyclic compounds possessing a chiral quaternary carbon center were obtained in high yields with high ees. In this cyclization, a Rh-C(sp(2)) bond in the rhodacyclopentene intermediate, which was formed by enantioselective oxidative cycloaddition of enynes to a chiral rhodium(I) complex, was intramolecularly cleaved by sigma-bond metathesis of a tethered O-H bond in the substrate. Furthermore, it was found that the cyclic compounds were obtained with high ees even when the starting materials having a racemic secondary alcohol moiety were used in this reaction. |
| Rights: | This is the peer reviewed version of the following article: Angewandte chemie-international edition,58(26),8736-8739,(2019), which has been published in final form at https://doi.org/10.1002/anie.201902832 . 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/2115/78679 |
| 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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