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Cationic Iridium/Chiral Bisphosphine-Catalyzed Enantioselective Hydroacylation of Ketones

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Title: Cationic Iridium/Chiral Bisphosphine-Catalyzed Enantioselective Hydroacylation of Ketones
Authors: Shirai, Tomohiko Browse this author →KAKEN DB
Iwasaki, Tomoya Browse this author
Kanemoto, Kazuya Browse this author →KAKEN DB
Yamamoto, Yasunori Browse this author →KAKEN DB
Keywords: hydroacylation
C-H activation
cationic iridium
Issue Date: 23-Jun-2020
Publisher: Wiley-Blackwell
Journal Title: Chemistry-an asian journal
Volume: 15
Issue: 12
Start Page: 1858
End Page: 1862
Publisher DOI: 10.1002/asia.202000386
Abstract: 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.
Rights: This is the peer reviewed version of the following article:, 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.
Type: article (author version)
Appears in Collections:創成研究機構 (Creative Research Institution) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 山本 靖典

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