74958-71-7Relevant articles and documents
Thiourea Derivative of 2-[(1 R)-1-Aminoethyl]phenol: A Flexible Pocket-like Chiral Solvating Agent (CSA) for the Enantiodifferentiation of Amino Acid Derivatives by NMR Spectroscopy
Balzano, Federica,Micheletti, Cosimo,Recchimurzo, Alessandra,Uccello-Barretta, Gloria
, p. 5342 - 5350 (2020/05/19)
Thiourea derivatives of 2-[(1R)-1-aminoethyl]phenol, (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol, (1R,2R)-(1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol, and (R)-1-phenylethanamine have been compared as chiral solvating agents (CSAs) for the enantiodiscrimination of derivatized amino acids using nuclear magnetic resonance (NMR) spectroscopy. Thiourea derivative, prepared by reacting 2-[(1R)-1-aminoethyl]phenol with benzoyl isothiocyanate, constitutes an effective CSA for the enantiodiscrimination of N-3,5-dinitrobenzoyl (DNB) derivatives of amino acids with free or derivatized carboxyl functions. A base additive 1,4-diazabicyclo[2.2.2]octane(DABCO)/N,N-dimethylpyridin-4-amine (DMAP)/NBu4OH) is required both to solubilize amino acid derivatives with free carboxyl groups in CDCl3 and to mediate their interaction with the chiral auxiliary to attain efficient differentiation of the NMR signals of enantiomeric substrates. For ternary systems CSA/substrate/DABCO, the chiral discrimination mechanism has been ascertained through the NMR determination of complexation stoichiometry, association constants, and stereochemical features of the diastereomeric solvates.
A Chiral Stationary Phase for the Facile Resolution of Amino Acids, Amino Alcohols, and Amines as the N-3,5-Dinitrobenzoyl Derivatives
Pirkle, William H.,Hyun, Myung Ho
, p. 3043 - 3046 (2007/10/02)
A chiral stationary phase derived from α-(6,7-dimethyl-1-naphthyl)isobutylamine is quite effective for the liquid chromatographic separation of the enantiomers of the N-3,5-dinitrobenzoyl derivatives of α-amino acids, their esters and amides, amino alcoho
