Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 15, Pages 8688-8694Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00873
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Funding
- National Natural Science Foundation of China [21502188, 21362014]
- Open Project Program of Key Laboratory of Functional Small Organic Molecule, Ministry of Education, Jiangxi Normal University [KLFS-KF-201705]
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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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