Отправить статью по E-mail Stereoinversion in the diastereoselective acylation of benzoxazine derivatives with 2-aryloxypropionyl chlorides
- Авторы: Vakarov S.1, Korolyova M.1, Gruzdev D.1,2, Pervova M.1, Levit G.1,2, Krasnov V.1
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Учреждения:
- 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
- Выпуск: Том 68, № 6 (2019)
- Страницы: 1257-1263
- Раздел: 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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Аннотация
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.
Об авторах
S. Vakarov
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Автор, ответственный за переписку.
Email: savakarov@ios.uran.ru
Россия, 22/20 ul. S. Kovalevskoi, Ekaterinburg, 620990
M. Korolyova
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: savakarov@ios.uran.ru
Россия, 22/20 ul. S. Kovalevskoi, Ekaterinburg, 620990
D. 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
Россия, 22/20 ul. S. Kovalevskoi, Ekaterinburg, 620990; 19 ul. Mira, Ekaterinburg, 620002
M. Pervova
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: savakarov@ios.uran.ru
Россия, 22/20 ul. S. Kovalevskoi, Ekaterinburg, 620990
G. 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
Россия, 22/20 ul. S. Kovalevskoi, Ekaterinburg, 620990; 19 ul. Mira, Ekaterinburg, 620002
V. Krasnov
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
Email: savakarov@ios.uran.ru
Россия, 22/20 ul. S. Kovalevskoi, Ekaterinburg, 620990
