Synthesis of chiral crownophanes having two phenolic groups via tandem claisen rearrangement and their chiral recognition

Asymmetric crownophanes having a chiral binaphthyl unit and two phenolic hy droxyl groups were thermally synthesized from the corresponding macrocyclic ethers via tandem Claisen rearrangement. Circular dichroism (CD) spectrosc opic studies and HPLC experiments confirmed that little racemization of the se crownophanes occurred during the thermal rearrangement. The association constants for the interaction of the chiral crownophanes with the enantiome rs of phenylethylamine, phenylglycinol, and phenylalaninol were determined by a H-1 NMR titration method in CD2Cl2. As a result, the 27 membered crown ophane has some chiral recognition for phenylglycinol.