Rhodium(I)-Catalyzed Enantioselective Cyclization of Enynes through Site-Selective C(sp3)-H Bond Activation Triggered by Formation of Rhodacycle

Oonishi, Yoshihiro; Sakamoto, Shunki; Agata, Shuya et al.

Synthesis, 2021, 53(17), 2976-2983

Permalink : https://hdl.handle.net/2115/84694

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アクセス権
open access
URI
https://hdl.handle.net/2115/84694
タイトル
Rhodium(I)-Catalyzed Enantioselective Cyclization of Enynes through Site-Selective C(sp3)-H Bond Activation Triggered by Formation of Rhodacycle
著者
Oonishi, Yoshihiro ; Sakamoto, Shunki ; Agata, Shuya ; Sato, Yoshihiro
e-Rad_Researcher
70399955
著者名
Oonishi, Yoshihiro
著者名
Sakamoto, Shunki
著者名
Agata, Shuya
e-Rad_Researcher
90226019
著者名
Sato, Yoshihiro
言語
英語
キーワード
rhodium
enantioselective cyclization
C(sp3)-H bond activation
alkene
alkyne
enyne
発行日
2021-03-30
出版者
Georg Thieme Verlag
収録物名
Synthesis
巻(号)
53(17)
ページ
2976-2983
抄録
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.
資源タイプ
学術雑誌論文
出版タイプ
Accepted Manuscript
権利情報
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
PISSN
0039-7881
関連情報 (isVersionOf)
出版社版DOI
https://doi.org/10.1055/a-1469-7408