Synthesis, Rapid Resolution, and Determination of Absolute Configuration of Racemic 2,2'-Binaphthyldiyl Crown Ethers and Analogues via β-Cyclodextrin Complexation

Article abstract of DOI:10.1021/jo00350a025

Twenty racemic and four diastereomeric 2,2'-binaphthyldiyl crown ethers and analogues were synthesized.Chiral interactions between these compounds and immobilized β-cyclodextrin were examined.Thirteen of the enantiomeric pairs and two of the diastereomers were successfully resolved.It was found that relatively small changes in the structure of these compounds could have large effects on chiral recognition.In general, the (-)-S enantiomers formed stronger inclusion complexes with β-cyclodextrin than did the (+)-R enantiomers.