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Kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and its structural analogs by using 2-arylpropionyl chlorides

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Chemistry of Heterocyclic Compounds Aims and scope

Acylation of 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methylindoline with the acyl chlorides of naproxen, ibuprofen, and 2-phenylpropionic acid has been found to lead to efficient kinetic resolution with predominant formation of the (S,S)-(R,R)-diastereoisomers. The highest acylation stereoselectivity was found in toluene at -20°C. No significant kinetic resolution of N-(sec-butyl)aniline and 2-methylpiperidine was achieved by using 2-arylpropionyl chlorides.

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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, 620990, Russia

    E. N. Chulakov, G. L. Levit, A. A. Tumashov, L. Sh. Sadretdinova & V. P. Krasnov

Authors
  1. E. N. Chulakov
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  2. G. L. Levit
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  3. A. A. Tumashov
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  4. L. Sh. Sadretdinova
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  5. V. P. Krasnov
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Correspondence to V. P. Krasnov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 779-788, May, 2012.

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Chulakov, E.N., Levit, G.L., Tumashov, A.A. et al. Kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and its structural analogs by using 2-arylpropionyl chlorides. Chem Heterocycl Comp 48, 724–732 (2012). https://doi.org/10.1007/s10593-012-1051-x

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  • DOI: https://doi.org/10.1007/s10593-012-1051-x

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