<i>N</i>-TOSYL-(<i>S</i>)-PROLYL CHLORIDE IN KINETIC RESOLUTION OF RACEMIC HETEROCYCLIC AMINES

Authors

  • Д. А. Груздев I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
  • С. А. Вакаров I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
  • Г. Л. Левит I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences
  • В. П. Краснов I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

DOI:

https://doi.org/10.1007/988

Keywords:

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

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

Author Biographies

Д. А. Груздев, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Дмитрий Андреевич Груздев

Лаборатория асимметрического синтеза, научный сотрудник(Laboratory of Asymmetric Synthesis, Researcher)

С. А. Вакаров, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Сергей Анатольевич Вакаров

Лаборатория асимметрического синтеза, аспирант(Laboratory of Asymmetric Synthesis, Ph.D. Student)

Г. Л. Левит, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Галина Львовна Левит

Лаборатория асимметрического синтеза, ведущий научный сотрудник(Laboratory of Asymmetric Synthesis, Leading Researcher)

В. П. Краснов, I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Виктор Павлович Краснов

Лаборатория асимметрического синтеза, заведующий лабораторией(Laboratory of Asymmetric Synthesis, Head of Laboratory)

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Published

2013-11-22

Issue

No. 12 (2013)

Section

Original Papers