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Chiral Carboxylic Acid Enabled Achiral Rhodium(III)-Catalyzed Enantioselective C-H Functionalization

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Title: Chiral Carboxylic Acid Enabled Achiral Rhodium(III)-Catalyzed Enantioselective C-H Functionalization
Authors: Lin, Luqing Browse this author
Fukagawa, Seiya Browse this author
Sekine, Daichi Browse this author
Tomita, Eiki Browse this author
Yoshino, Tatsuhiko Browse this author →KAKEN DB
Matsunaga, Shigeki Browse this author →KAKEN DB
Keywords: amines
asymmetric catalysis
C-H activation
carboxylic acids
rhodium
Issue Date: 10-Sep-2018
Publisher: Wiley-Blackwell
Journal Title: Angewandte chemie-international edition
Volume: 57
Issue: 37
Start Page: 12048
End Page: 12052
Publisher DOI: 10.1002/anie.201807610
PMID: 30039561
Abstract: Reported is an achiral (CpRhIII)-Rh-x/chiral carboxylic acid catalyzed asymmetric C-H alkylation of diarylmethanamines with a diazomalonate, followed by cyclization and decarboxylation to afford 1,4-dihydroisoquinolin-3(2H)-one. Secondary alkylamines as well as nonprotected primary alkylamines underwent the transformation with high enantioselectivities (up to 98.5:1.5 e.r.) by using a newly developed chiral carboxylic acid as the sole source of chirality to achieve enantioselective C-H cleavage by a concerted metalation-deprotonation mechanism.
Rights: This is the peer-reviewed version of the following article: L.Lin, et al. / Chiral Carboxylic Acid Enabled Achiral Rhodium(III)-Catalyzed Enantioselective C-H Functionalization. Angewandte chemie-international edition, 57(37), 12048-12052, 2018, which has been published in final form at 10.1002/anie.201807610. This article may be used for non-commercial purposes in accordance with Wiley-VCH Terms and Conditions for Self-Archiving.
Type: article (author version)
URI: http://hdl.handle.net/2115/75430
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 吉野 達彦

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