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N-TOSYL-(S)-PROLYL CHLORIDE IN KINETIC RESOLUTION OF RACEMIC HETEROCYCLIC AMINES

Д. А. Груздев, С. А. Вакаров, Г. Л. Левит, В. П. Краснов
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Abstract


The kinetic resolution of racemic heterocyclic amines via acylation with N-tosyl-(S)-prolyl chloride was systematically investigated. It was established that racemic mixtures of aromatic amines could be resolved with high efficiency, while the acylation of 2- and 3-methylpiperidines occurred with low diastereoselectivity. A method for the preparation of enantiomerically pure (3R)-7,8-difluoro-3-methyl-3,4‑dihydro-2H-[1,4]benzoxazine was developed.

How to Cite
Gruzdev, D. A.; Vakarov, S. A.; Levit, G. L.; Krasnov, V. P. Chem. Heterocycl. Compd. 2014, 49, 1795. [Khim. Geterotsikl. Soedin. 2013, 1936.]

For this article in the English edition see DOI 10.1007/s10593-014-1432-4


Keywords


amines; (3R)-7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine; N-tosyl-(S)-proline; acylation; diastereoisomers; kinetic resolution; stereoselectivity

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