| Autor: |
Chulakov, E. N., Korolyova, M. A., Tumashov, A. A., Kodess, M. I., Levit, G. L., Krasnov, V. P. |
| Zdroj: |
Russian Chemical Bulletin; Dec2023, Vol. 72 Issue 12, p2938-2947, 10p |
| Abstrakt: |
A comparative study of the kinetic resolution of racemic 6-methoxy-, 6-nitro-, and 6-chloro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazines with (S)-naproxen acyl chloride, N-phthaloyl-(S)-leucyl chloride, and O-phenyl-(R)-lactyl chloride was carried out. The selectivity factors in the kinetic resolution of racemic amines with (S)-naproxen acyl chloride and O-phenyl-(R)-lactyl chloride were higher compared to N-phthaloyl-(S)-leucyl chloride. The factors responsible for the stereodifferentiation in the kinetic resolution of racemic dihydrobenzoxazines containing groups with different electronic properties were explained based on DFT calculations. Stacking interactions between aromatic moieties in the transition state were demonstrated to play a key role in the stereodifferentiation. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
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