602297-58-5Relevant academic research and scientific papers
Kinetic resolution of heterocyclic amines by reaction with optically active acid chlorides. The effect of reaction conditions on the diastereoselectivity of acylation of (±)-3-methyl-2,3-dihydro-4H-1,4-benzoxazine
Krasnov,Levit,Korolyova,Bukrina,Sadretdinova,Andreeva,Charushin,Chupakhin
, p. 1253 - 1256 (2004)
The influence of the reaction conditions (solvent, base) on the diastereoselectivity of acylation of (±)-3-methyl-2,3-dihydro-4H-1,4- benzoxazine with (S)-naproxen and N-tosyl-(S)-proline chlorides was studied. The highest diastereoselectivity was observe
N-tosyl-(S)-prolyl chloride in kinetic resolution of racemic heterocyclic amines
Gruzdev,Vakarov,Levit,Krasnov
, p. 1795 - 1807 (2014/05/06)
The kinetic resolution of racemic heterocyclic amines via acylation with N-tosyl-(S)-prolyl chloride was systematically investigated. It was established that racemic mixtures of aromatic amines could be resolved with high efficiency, while the acylation of 2- and 3-methylpiperidines occurred with low diastereoselectivity. A method for the preparation of enantiomerically pure (3R)-7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine was developed.
Diastereoselective acylation of racemic heterocyclic amines with N-tosyl-(S)-prolyl chloride and its structural analogs
Vakarov,Gruzdev,Chulakov,Sadretdinova, L. Sh.,Ezhikova,Kodess,Levit,Krasnov
, p. 838 - 855 (2014/11/08)
A comparative study on the kinetic resolution of racemic amines (2,3-dihydro-4H-1,4-benzoxazine and 1,2,3,4-tetrahydroquinoline derivatives) via diastereoselective acylation with N-tosyl-(S)-prolyl chloride and its structural analogs was performed. The effect of resolving agent structure on the stereoselectivity of heterocyclic amine acylation was examined. The highest stereoselectivity was achieved in the case of acylation with acyl chlorides bearing a conformationally restricted pyrrolidine ring and an aromatic substituent in the protecting group at the nitrogen atom.
Diastereoselective acylation of racemic heterocyclic amines with N-tosyl-(s)-prolyl chloride and its structural analogs
Vakarov,Gruzdev,Chulakov,Sadretdinova,Ezhikova,Kodess,Levit,Krasnov
, p. 838 - 855 (2015/09/28)
A comparative study on the kinetic resolution of racemic amines (2,3-dihydro-4H-1,4-benzoxazine and 1,2,3,4-tetrahydroquinoline derivatives) via diastereoselective acylation with N-tosyl-(S)-prolyl chloride and its structural analogs was performed. The effect of resolving agent structure on the stereoselectivity of heterocyclic amine acylation was examined. The highest stereoselectivity was achieved in the case of acylation with acyl chlorides bearing a conformationally restricted pyrrolidine ring and an aromatic substituent in the protecting group at the nitrogen atom.
Kinetic resolution of (±)-2,3-dihydro-3-methyl-4H-1,4-benzoxazine, (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline using N-tosyl-(S)-prolyl chloride
Krasnov, Victor P.,Levit, Galina L.,Bukrina, Iraida M.,Andreeva, Irina N.,Sadretdinova, Liliya Sh.,Korolyova, Marina A.,Kodess, Mikhail I.,Charushin, Valery N.,Chupakhin, Oleg N.
, p. 1985 - 1988 (2007/10/03)
Acylation of racemic 2,3-dihydro-3-methyl-4H-1,4-benzoxazine, 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methylindoline with N-tosyl-(S)-prolyl chloride resulted in their kinetic resolution with the predominant formation of (R,S)-diastereoisomeric amides,
