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Organocatalytic Asymmetric Reduction of Fluorinated Alkynyl Ketimines
Mu-Wang Chen1, Qin Yang1,2, Zhihong Deng1
1Key Laboratory of Small Functional Organic Molecule, Ministry of Education and College of Chemistry , Jiangxi Normal University , Nanchang , Jiangxi 330022 , China.
Abstract:
Highly chemoselective catalytic transfer hydrogenation of fluorinated alkynyl ketimines has been achieved by employing chiral phosphoric acid as a catalyst with benzothiazoline as a hydride source, providing the corresponding chiral fluorinated propargylamines in good yields and excellent enantioselectivities. In addition, iodocyclization of fluorinated propargylamine affords chiral 3-iodo-2-(trifluoromethyl)-1,2-dihydroquinoline, which can be easily converted to 2-(trifluoromethyl)- 1,2-dihydroquinoline derivatives with the selective COX-2 inhibitory activity.
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