Journal
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
Volume 50, Issue 6, Pages 838-855Publisher
SPRINGER
DOI: 10.1007/s10593-014-1538-8
Keywords
acyl chlorides; proline; racemic amines; acylation; diastereoselectivity; kinetic resolution
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Funding
- Russian Foundation for Basic Research [13-03-00674, 13-03-12188]
- Ural Branch of the Russian Academy of Sciences [12-P-3-1030]
- Grants Council of the President of the Russian Federation [NSh-3656.2014.3]
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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.
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