D. Gruzdev, E. Chulakov, G. Levit
Oct 15, 2013
Citations
0
Influential Citations
21
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract The acylative kinetic resolution of racemic 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline, 7,8-difluoro-3,4-dihydro-3-methyl-2 H -[1,4]benzoxazine, and their non-fluorinated analogues with ( S )-naproxen and N -phthaloyl-( S )-amino acyl chlorides has been carried out. It has been shown that the presence of fluorine atoms in the aromatic fragment of a heterocyclic amine results in the increasing stereoselectivity of acylation with ( S )-naproxen acyl chloride and in a decrease in the efficiency of acylative kinetic resolution using N -phthaloyl-( S )-amino acyl chlorides. A method for the preparation of enantiopure ( S )-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline ( ee >99%) was developed.