Synthesis of the proton-ionizable lariat crown ether and chiral recognition of primary amines

Article abstract of DOI:10.1016/S0040-4020(02)00074-1

An optically active proton-ionizable lariat crown ether derivative 2 was prepared. Host 2 displays enantiomeric selectivity toward phenylglycinol (K_large/K_small=3.2) and phenylalaninol (K_large/K_small=1.7). The key intermediate 1 was synthesized in two steps from commercially available binaphthol in 30% yield.