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Synthesis of chiral 1-(imidazol-2-yl)alkanamines using neomenthanethiol as a chiral auxiliary

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Abstract

Diastereomeric N-(imidazol-2-ylmethylidene)neomenthane-3-sulfinamides were obtained from enantiomerically pure neomenthanethiol in three steps. The compounds obtained added Grignard reagents at the C=N bond. After separation of diastereomers, an acid resolution gave enantiomerically pure primary 1-(imidazol-2-yl)alkanamines. In this scheme, the neomenthane fragment played the role of a chiral auxiliary.

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Authors and Affiliations

  1. Institute of Chemistry, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences, 48 ul. Pervomaiskaya, 167982, Syktyvkar, Russian Federation

    D. V. Sudarikov, Yu. V. Krymskaya, S. A. Rubtsova & A. V. Kutchin

  2. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 ul. S. Kovalevskoi, 620219, Ekaterinburg, Russian Federation

    P. A. Slepukhin

  3. Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 prosp. Lenina, 620000, Ekaterinburg, Russian Federation

    P. A. Slepukhin

Authors
  1. D. V. Sudarikov
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  2. Yu. V. Krymskaya
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  3. P. A. Slepukhin
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  4. S. A. Rubtsova
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  5. A. V. Kutchin
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Correspondence to D. V. Sudarikov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1566—1573, June, 2016.

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Sudarikov, D.V., Krymskaya, Y.V., Slepukhin, P.A. et al. Synthesis of chiral 1-(imidazol-2-yl)alkanamines using neomenthanethiol as a chiral auxiliary. Russ Chem Bull 65, 1566–1573 (2016). https://doi.org/10.1007/s11172-016-1483-z

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  • DOI: https://doi.org/10.1007/s11172-016-1483-z

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