Email this article Kinetic resolution of racemic 3-tert-butyl-3,4-dihydro-2H-[1,4]benzoxazine via acylation with chiral acyl chlorides
- Authors: Vakarov S.A.1, Gruzdev D.A.1,2, Chulakov E.N.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
- Ural Federal University named after the first President of Russia B. N. Yeltsin
- Issue: Vol 68, No 4 (2019)
- Pages: 841-847
- Section: Full Article
- URL: https://ogarev-online.ru/1066-5285/article/view/243355
- DOI: https://doi.org/10.1007/s11172-019-2494-3
- ID: 243355
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Abstract
A comparative study of the kinetic resolution of racemic 3-tert-butyl-3,4-dihydro-2H-[1,4]-benzoxazine through the acylation by various chiral acyl chlorides was carried out. A preparative method for obtaining enantiomerically pure (S)-3-tert-butyl-3,4-dihydro-2H-[1,4]benzoxazine can be based on the acylation with N-phthaloyl-(S)-phenylalanyl or (R)-2-phenoxypropionyl chlorides, followed by the acid hydrolysis of the corresponding diastereomerically pure amides.
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
D. A. Gruzdev
I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; 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
E. N. Chulakov
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; 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
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