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Diastereoselective Acylation of Racemic Heterocyclic Amines with N-Tosyl-(S)-Prolyl Chloride and its Structural Analogs

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Chemistry of Heterocyclic Compounds Aims and scope

A comparative study on the kinetic resolution of racemic amines (2,3-dihydro-4H-1,4-benzoxazine and 1,2,3,4-tetrahydroquinoline derivatives) via diastereoselective acylation with N-tosyl-(S)-prolyl chloride and its structural analogs was performed. The effect of resolving agent structure on the stereoselectivity of heterocyclic amine acylation was examined. The highest stereoselectivity was achieved in the case of acylation with acyl chlorides bearing a conformationally restricted pyrrolidine ring and an aromatic substituent in the protecting group at the nitrogen atom.

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Authors and Affiliations

  1. I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 S. Kovalevskoi St. / 20 Akademicheskaya St., Yekaterinburg, 620137, Russia

    S. A. Vakarov, D. A. Gruzdev, E. N. Chulakov, L. Sh. Sadretdinova, M. A. Ezhikova, M. I. Kodess, G. L. Levit & V. P. Krasnov

Authors
  1. S. A. Vakarov
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  2. D. A. Gruzdev
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  3. E. N. Chulakov
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  4. L. Sh. Sadretdinova
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  5. M. A. Ezhikova
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  6. M. I. Kodess
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  7. G. L. Levit
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  8. V. P. Krasnov
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Corresponding author

Correspondence to D. A. Gruzdev.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 908-927, June, 2014.

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Vakarov, S.A., Gruzdev, D.A., Chulakov, E.N. et al. Diastereoselective Acylation of Racemic Heterocyclic Amines with N-Tosyl-(S)-Prolyl Chloride and its Structural Analogs. Chem Heterocycl Comp 50, 838–855 (2014). https://doi.org/10.1007/s10593-014-1538-8

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  • DOI: https://doi.org/10.1007/s10593-014-1538-8

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