Email this article Synthesis of chiral 1-(imidazol-2-yl)alkanamines using neomenthanethiol as a chiral auxiliary
- Authors: Sudarikov D.V.1, Krymskaya Y.V.1, Slepukhin P.A.2,3, Rubtsova S.A.1, Kutchin A.V.1
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Affiliations:
- Institute of Chemistry, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences
- 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 65, No 6 (2016)
- Pages: 1566-1573
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/238418
- DOI: https://doi.org/10.1007/s11172-016-1483-z
- ID: 238418
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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.
About the authors
D. V. Sudarikov
Institute of Chemistry, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences
Author for correspondence.
Email: sudarikov-dv@chemi.komisc.ru
Russian Federation, 48 ul. Pervomaiskaya, Syktyvkar, 167982
Yu. V. Krymskaya
Institute of Chemistry, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences
Email: sudarikov-dv@chemi.komisc.ru
Russian Federation, 48 ul. Pervomaiskaya, Syktyvkar, 167982
P. A. Slepukhin
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: sudarikov-dv@chemi.komisc.ru
Russian Federation, 22 ul. S. Kovalevskoi, Ekaterinburg, 620219; 51 prosp. Lenina, Ekaterinburg, 620000
S. A. Rubtsova
Institute of Chemistry, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences
Email: sudarikov-dv@chemi.komisc.ru
Russian Federation, 48 ul. Pervomaiskaya, Syktyvkar, 167982
A. V. Kutchin
Institute of Chemistry, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences
Email: sudarikov-dv@chemi.komisc.ru
Russian Federation, 48 ul. Pervomaiskaya, Syktyvkar, 167982
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