Chiral trans-1,2-diaminocyclohexane derivatives as chiral solvating agents for carboxylic acids

Journal of Chemical Sciences

Mariappan Periasamy1¹  Meduri Padmaja¹  Manasi Dalai¹ 

[1] School of Chemistry, University of Hyderabad, Central University P.O., Hyderabad 500 046$$

关键词: Chiral 1;    2-cyclohexyl diamines;    macrocyclic amines;    chiral solvating agents;    enantiomeric purity;    chiral carboxylic acids.;   

DOI  :  

来源: Indian Academy of Sciences

【 摘 要 】

Efficient use of the readily accessible chiral 𝐶2-symmetric acyclic diamines (1-2) as well as macrocyclic amines (3-5) containing trans-1,2-diaminocyclohexyl moiety as chiral solvating agents (CSA) for the determination of enantiomeric excess of representative carboxylic acids (6-7) and an amino acid derivative (8) is illustrated. The enantiomeric composition of different carboxylic acids estimated here by the 1H NMR method, based on the integration of the corresponding methine proton signals are in good correlation with that determined using HPLC method. The data are in accordance with the formation of multimolecular diastereomeric complexes in solution, which render good splitting of NMR signals for the enantiomers of representative carboxylic acids as well as for 𝑁-Ts-phenylglycine (up to 𝛥𝛥𝛿 = 0.295 ppm, 118 Hz).

【 授权许可】

Unknown