Email this article Stereoinversion in the diastereoselective acylation of benzoxazine derivatives with 2-aryloxypropionyl chlorides
- Authors: Vakarov S.A.1, Korolyova M.A.1, Gruzdev D.A.1,2, Pervova M.G.1, Levit G.L.1,2, Krasnov V.P.1
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Affiliations:
- I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
- Institute of Chemical Engineering, Ural Federal University named after the first President of Russia B. N. Yeltsin
- Issue: Vol 68, No 6 (2019)
- Pages: 1257-1263
- Section: Full Article
- URL: https://journals.rcsi.science/1066-5285/article/view/243411
- DOI: https://doi.org/10.1007/s11172-019-2550-z
- ID: 243411
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Abstract
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-CH2Cl2-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.
About the authors
S. A. Vakarov
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Author for correspondence.
Email: savakarov@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoi, Ekaterinburg, 620990
M. A. Korolyova
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: savakarov@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoi, Ekaterinburg, 620990
D. A. Gruzdev
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; Institute of Chemical Engineering, Ural Federal University named after the first President of Russia B. N. Yeltsin
Email: savakarov@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoi, Ekaterinburg, 620990; 19 ul. Mira, Ekaterinburg, 620002
M. G. Pervova
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: savakarov@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoi, Ekaterinburg, 620990
G. L. Levit
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; Institute of Chemical Engineering, Ural Federal University named after the first President of Russia B. N. Yeltsin
Email: savakarov@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoi, Ekaterinburg, 620990; 19 ul. Mira, Ekaterinburg, 620002
V. P. Krasnov
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: savakarov@ios.uran.ru
Russian Federation, 22/20 ul. S. Kovalevskoi, Ekaterinburg, 620990
