Enantiomeric separation of racemic 4-aryl-1,4-dihydropyridines and 4-aryl-1,2,3,4-tetrahydropyrimidines on a chiral tetraproline stationary phase.
Enantiomeric separation of racemic 4-aryl-1,4-dihydropyridines and 4-aryl-1,2,3,4-tetrahydropyrimidines on a chiral tetraproline stationary phase.
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在手性四脯氨酸固定相上对外消旋 4-芳基-1,4-二氢吡啶和 4-芳基-1,2,3,4-四氢嘧啶进行对映体分离。
作者：
Dai,Zhi;PittmanJr,CharlesU;Li,Tingyu
The chromatographic chiral resolution of 4‐aryl‐1,4‐dihydropyridines (1–32), 4‐aryl‐2‐thioxo‐1,2,3,4‐tetrahydropyrimidines (33–38), and 4‐aryl‐2‐oxo‐1,2,3,4‐tetrahydropyrimidines (39–41) was studied on a tetraproline‐immobilized chiral column synthesized in our lab. This tetraproline chiral stationary phase can resolve most of these compounds. The 4‐aryl‐2‐thioxo‐1,2,3,4‐tetrahydropyrimidines (33–38) and 4‐aryl‐2‐oxo‐1,2,3,4‐tetrahydropyrimidines (39–41) were more efficiently resolved than the racemic 4‐aryl‐1,4‐dihydropyridines on the tetraproline chiralstationary phase. Analytes with 5,5‐dimethyl groups (39–41) were less efficiently resolved than analytes without 5,5‐dimethyl substituents (1–16). The 4‐aryl‐2‐oxo‐1,2,3,4‐tetrahydropyrimidines (39–41) without a sulfur atom were much more efficiently resolved than 4‐aryl‐2‐thioxo‐1,2,3,4‐tetrahydropyrimidines (33–38). No obvious electronic effects on the resolution of any of these analytes (1–41) were observed on the tetraproline chiral stationary phase. The tetraproline chiral stationary phase separated enantiomers mainly via hydrogen bonding interactions. Chirality, 2013. © 2013 Wiley Periodicals, Inc.
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