A 10 A comparative study on the acylative kinetic resolution of racemic fluorinated and non-fluorinated 2-methyl-1,2,3,4-tetrahydroquinolines and 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines [Electronic resource] / D. A. Gruzdev, E. N. Chulakov, G. L. Levit, M. A. Ezhikova, M. I. Kodess, V. P. Krasnov // Tetrahedron: Asymmetry . - 2013. - Vol.24, №19. - С. 1240-1246. - Bibliogr. : p. 1246 (21 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): RACEMIC FLUORINATED -- 1,2,3,4-TETRAHYDROQUINOLINES -- BENZOXAZINES Аннотация: The acylative kinetic resolution of racemic 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline, 7,8-difluoro-3,4-dihydro-3-methyl-2H-[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 \\\\expert2\\NBO\\Tetrahedron Asymmetry\\2013, in Press, Corr. Proof, 4 Sept.pdf |