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


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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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D. Sudarikov

Institute of Chemistry, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences

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Email: sudarikov-dv@chemi.komisc.ru
俄罗斯联邦, 48 ul. Pervomaiskaya, Syktyvkar, 167982

Yu. Krymskaya

Institute of Chemistry, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences

Email: sudarikov-dv@chemi.komisc.ru
俄罗斯联邦, 48 ul. Pervomaiskaya, Syktyvkar, 167982

P. 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
俄罗斯联邦, 22 ul. S. Kovalevskoi, Ekaterinburg, 620219; 51 prosp. Lenina, Ekaterinburg, 620000

S. Rubtsova

Institute of Chemistry, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences

Email: sudarikov-dv@chemi.komisc.ru
俄罗斯联邦, 48 ul. Pervomaiskaya, Syktyvkar, 167982

A. Kutchin

Institute of Chemistry, Komi Scientific Center of the Ural Branch of the Russian Academy of Sciences

Email: sudarikov-dv@chemi.komisc.ru
俄罗斯联邦, 48 ul. Pervomaiskaya, Syktyvkar, 167982

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