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

H.A. Samimi^a, M. Mamaghani^a,, K. Tabatabeian^a and H.R. Bijanzadeh^b*

^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

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

H.A. Samimi^a, M. Mamaghani^a,, K. Tabatabeian^a and H.R. Bijanzadeh^b*

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