Novel C2-symmetric macrocycles bearing diamide-diester groups: synthesis and enantiomeric recognition for primary alkyl ammonium salts.
We synthesized a series of novel macrocycles with diamide-diester groups (S,S)-1, (S,S)-2, (S,S)-3, and (R,R)-1, derived from dimethyloxalate and amino alcohols by high dilution technique, and evaluated enantiomeric recognition properties of these macrocycles toward primary alkyl ammonium salts by 1H NMR titration. Taking into account the host employed, important differences were observed in the Ka values of (R)-Am and (S)-Am for (S,S)-1 and (R,R)-1 hosts, KS/KR = 5.55 and KR/KS = 3.65, Delta Delta Go = 0.43 and -0.32 kJ mol-1, respectively. There seems a general tendency for the host to include the guests with the same absolute configuration.
Sunkur
Murat
M
Chemistry Department, University of Dicle, Faculty of Art and Science, 21280-Diyarbakir, Turkey.
Baris
Deniz
D
Hosgoren
Halil
H
Togrul
Mahmut
M
D000605:Amino Alcohols / Q000737:chemistry; D003958:Diamide / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008968:Molecular Conformation; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D012015:Reference Standards; D013237:Stereoisomerism
D000605:Amino Alcohols; D004952:Esters; D047028:Macrocyclic Compounds; D000644:Quaternary Ammonium Compounds; D003958:Diamide