Tetrahedron: Asymmetry

The effect of substituents on the chiral solvating properties of (S)-1, 6-dialkylpiperazine-2, 5-diones

Č Malavašič, B Stanovnik, J Wagger, J Svete

Index: Malavasic, Crt; Stanovnik, Branko; Wagger, Jernej; Svete, Jurij Tetrahedron Asymmetry, 2011 , vol. 22, # 12 p. 1364 - 1371

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Abstract

The effect of substituents on the chiral solvating properties of 13 different (S)-1, 6- dialkylpiperazine-2, 5-diones (S)-1a–m and five (3S, 6S)-1, 3, 6-trialkyl analogues (S, S)-1n– r was studied by NMR in CDCl3 with methyl (RS)-N-benzoylleucinate (RS)-2a as the model analyte. Most diketopiperazines exhibited typical resolution, ΔΔδRS-20∼ 0.1 ppm. Increased performance was observed with 6-CH2R substituted compounds (S)-1h–j. The ...