Synthesis of chiral monoaza-15-crown-5 ethers derivatives by a novel method and their useability on enantiomeric recognition on some chiral amines

Ill 2. SUMMARY i?-(-)-2-amino-l-butanol, which is widely used in the production of antituberculostatic etambutol, was derivatized to JV-benzyl-i?-(-)-2-amino-l-butanol, from which two chiral amino alcohol precursors were prepared by simply treating the derivative with ethylene oxide. Finally these chiral amino alcohols were reacted with various types of ditosylates to obtain 3 (three) chiral A^-benzyl mono-aza crown ethers. Host-guest complexes of these crown ethers with cc-phenylethyl and a- naphtylethyl ammonium perchlorate salts were prapared. All compounds synthesed and complexes were identified by chemical analysis, IR, *H NMR and I3C NMR. Crystal structures of complexes of some hosts with NaClÛ4 were also stadied by X-Ray diffraction.