Novel C2-symmetric macrocycles bearing diamide-diester groups: Synthesis and enantiomeric recognition for primary alkyl ammonium salts
MetadataShow full item record
CitationSünkür, M., Barış Cebe, D., Hoşgören, H., Toğrul, M. (2008). Novel C2-symmetric macrocycles bearing diamide-diester groups: Synthesis and enantiomeric recognition for primary alkyl ammonium salts. Journal of Organic Chemistry, 73 (7), pp. 2570–2575. https://doi.org/10.1021/jo702210c
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, ΔΔGo = 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.
SourceJournal of Organic Chemistry
The following license files are associated with this item: