Cationic Iridium/Chiral Bisphosphine-Catalyzed Enantioselective Hydroacylation of Ketones

Shirai, Tomohiko; Iwasaki, Tomoya; Kanemoto, Kazuya et al.

Chemistry-an asian journal, 2020, 15(12), 1858-1862

Permalink : https://hdl.handle.net/2115/81935

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アクセス権
open access
URI
https://hdl.handle.net/2115/81935
タイトル
Cationic Iridium/Chiral Bisphosphine-Catalyzed Enantioselective Hydroacylation of Ketones
著者
Shirai, Tomohiko ; Iwasaki, Tomoya ; Kanemoto, Kazuya ; Yamamoto, Yasunori
e-Rad_Researcher
80784644
著者名
Shirai, Tomohiko
著者名
Iwasaki, Tomoya
e-Rad_Researcher
90849100
著者名
Kanemoto, Kazuya
e-Rad_Researcher
30271646
著者名
Yamamoto, Yasunori
言語
英語
キーワード
hydroacylation
ketone
C-H activation
cationic iridium
enantioselective
発行日
2020-06-23
出版者
Wiley-Blackwell
収録物名
Chemistry-an asian journal
巻(号)
15(12)
ページ
1858-1862
抄録
A facile and convenient synthesis of the chiral phthalide framework catalyzed by cationic iridium was developed. The method utilized cationic iridium/bisphosphine-catalyzed asymmetric intramolecular carbonyl hydroacylation of 2-keto benzaldehydes to furnish the corresponding optically active phthalide products in good to excellent enantioselectivities (up to 98% ee). The mechanistic studies using a deuterium-labelled substrate suggested that the reaction involved an intramolecular carbonyl insertion mechanism to iridium hydride intermediate. In addition, we investigated the kinetic isotope effect (KIE) of intramolecular hydroacylation with deuterated substrate and determined that the C-H activation step is not included in the turnover-limiting step.
資源タイプ
学術雑誌論文
出版タイプ
Accepted Manuscript
権利情報
This is the peer reviewed version of the following article: https://onlinelibrary.wiley.com/doi/full/10.1002/asia.202000386, which has been published in final form at 10.1002/asia.202000386. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
PISSN
1861-4728
関連情報 (isVersionOf)
出版社版DOI
https://doi.org/10.1002/asia.202000386