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N-Tosyl-(S)-Prolyl Chloride in Kinetic Resolution of Racemic Heterocyclic Amines

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Chemistry of Heterocyclic Compounds Aims and scope

The kinetic resolution of racemic heterocyclic amines via acylation with N-tosyl-(S)-prolyl chloride was systematically investigated. It was established that racemic mixtures of aromatic amines could be resolved with high efficiency, while the acylation of 2- and 3-methylpiperidines occurred with low diastereoselectivity. A method for the preparation of enantiomerically pure (3R)-7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine was developed.

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The work was performed with financial support from the Russian Foundation for Basic Research (grants 12-03-31615, 12-03-33029, 13-03-00674), the Ural Branch of the Russian Academy of Sciences (project 12-P-3-1030), and the Grants Council of the President of the Russian Federation (grant NSh-3656.2014.3).

The authors are grateful to L. Sh. Sadretdinova for performing the HPLC analyses, and to Cand. Chem. Sci. M. I. Kodess for the recording of NMR spectra.

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Authors and Affiliations

  1. I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi St. / 20 Akademicheskaya St., Yekaterinburg, 620990, Russia

    D. A. Gruzdev, S. A. Vakarov, G. L. Levit & V. P. Krasnov

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  1. D. A. Gruzdev
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  2. S. A. Vakarov
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  3. G. L. Levit
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  4. V. P. Krasnov
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Correspondence to D. A. Gruzdev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1936-1950, December, 2013.

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Gruzdev, D.A., Vakarov, S.A., Levit, G.L. et al. N-Tosyl-(S)-Prolyl Chloride in Kinetic Resolution of Racemic Heterocyclic Amines. Chem Heterocycl Comp 49, 1795–1807 (2014). https://doi.org/10.1007/s10593-014-1432-4

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