KINETIC RESOLUTION OF RACEMIC 2-METHYL-1,2,3,4-TETRAHYDROQUINOLINE AND ITS STRUCTURAL ANALOGS BY USING 2-ARYLPROPIONYL CHLORIDES

Authors

  • Е. Н. Чулаков I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • Г. Л. Левит I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • А. А. Тумашов I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • Л. Ш. Садретдинова I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
  • В. П. Краснов I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences

DOI:

https://doi.org/10.1007/1192

Keywords:

2-arylpropionic acids, 2-methylindoline, 2-methyl-1, 2, 3, 4-tetrahydroquinoline, acyl chlorides, acylation, kinetic resolution

Abstract

Acylation of 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methylindoline with the acyl chlorides of naproxen, ibuprofen, and 2-phenylpropionic acid has been found to lead to efficient kinetic resolution with predominant formation of the (S,S)-(R,R)-diastereoisomers. The highest acylation stereoselectivity was found in toluene at -20°C. No significant kinetic resolution of N-(sec-butyl)aniline and 2-methylpiperidine was achieved by using 2-arylpropionyl chlorides.

Authors: E. N. Chulakov, G. L. Levit, A. A. Tumashov, L. Sh. Sadretdinova, and V. P. Krasnov.

English Translation in Chemistry of Heterocyclic Compounds, 2012, 48 (5), pp 724-732

http://link.springer.com/article/10.1007/s10593-012-1051-x

Downloads

Published

2013-11-20

Issue

No. 5 (2012)

Section

Original Papers