J. Iran. Chem. Soc., Vol. 7, No. 1 March 2010, pp.185~189.

Current location: JICS Archive > Vol. 7 > No. 1 > Articles : 21

Studies on the Synthesis and Dynamic NMR Properties of 2-(Benzylidene amino)-N-[(R)-2-hydroxy-2-methyl-1-phenylpropyl]acetamide

H.A. Samimia, M. Mamaghania,*, K. Tabatabeiana and H.R. Bijanzadehb

aDepartment of Chemistry, Faculty of Sciences, University of Guilan, P. O. Box 41335-1914, Rasht, Iran
bDepartment of Chemistry, Tarbiat Modaress University, Tehran, Iran

An efficient method was employed for the preparation of 2-(benzylideneamino)-N-[(R)-2-hydroxy-2-methyl-1-phenylpropyl] acetamide utilizing optically pure (R)-5,5-dimethyl-4-phenyloxazolidin-2-one. This product showed interesting dynamic NMR properties for the methylene protons adjacent to the azomethine group (G = 15.1 ± 0.1 kcal mol-1).

Keywords: Chiral azomethine, Azomethine ylide, Dynamic NMR, Chiral auxiliary

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