Stereoinversion in the diastereoselective acylation of benzoxazine derivatives with 2-aryloxypropionyl chlorides
Journal Article
·
· Russian Chemical Bulletin
- Ural Branch of the Russian Academy of Sciences, I. Ya. Postovsky Institute of Organic Synthesis (Russian Federation)
A comparative study of the kinetic resolution of racemic derivatives of 3,4-dihydro-3-methyl-2H-[1,4]benzoxazine using racemic 2-aryloxypropionyl chlorides was performed. It was found that the acylation of racemic amines with racemic 2-(1-naphthyloxy)propionyl chloride leads to amides enriched with (3R*,2′R*)-diastereomers, while the acylation with 2-phenoxypropionyl chloride gives predominantly (3R*,2′S*)-amides. Quantum chemical modeling of the process of kinetic resolution at the COSMO-CH{sub 2}Cl{sub 2}-B3LYP-D3-gCP/def2-TZVP//B3LYP-D3-gCP/def2-SVP level of theory was performed. The computational results are in a good agreement with the experimental data.
- OSTI ID:
- 22943138
- Journal Information:
- Russian Chemical Bulletin, Journal Name: Russian Chemical Bulletin Journal Issue: 6 Vol. 68; ISSN RCBUEY; ISSN 1066-5285
- Country of Publication:
- United States
- Language:
- English
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