2024-03-28T08:47:54Zhttps://eprints.lib.hokudai.ac.jp/dspace-oai/requestoai:eprints.lib.hokudai.ac.jp:2115/754302022-11-17T02:08:08Zhdl_2115_20044hdl_2115_124Chiral Carboxylic Acid Enabled Achiral Rhodium(III)-Catalyzed Enantioselective C-H FunctionalizationLin, LuqingFukagawa, SeiyaSekine, DaichiTomita, EikiYoshino, TatsuhikoMatsunaga, Shigekiaminesasymmetric catalysisC-H activationcarboxylic acidsrhodium460Reported 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.Wiley-BlackwellJournal Articleapplication/pdfhttp://hdl.handle.net/2115/75430https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/75430/1/WoS_85740_Yoshino.pdf1433-7851Angewandte chemie-international edition573712048120522018-09-10enginfo:pmid/30039561info:doi/10.1002/anie.201807610This 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.author