Preparation and enantiomer recognition behaviour of crown ethers containing cis-1-phenylcyclohexane-1,2-diol and trans-1,2-diphenylcyclohexane-1,2-diol as a chiral subunit

Abstract

Pig liver esterase-mediated hydrolysis of (±)-cis-2-acetoxy-1-phenylcyclohexanol 5 gave (+)-cis-1-phenylcyclohexane-1. 2-diol 4 of high optical purity, from which (–)-trans-1, 2-diphenylcyclohexane-1, 2-diol 8 has been prepared. Using these diols (+)-4 and (–)-8 as a chiral subunit, chiral crown ethers (–)-1, (–)-2 and (–)-3 have been prepared and their chiral recognition behaviour toward (±)-1, 2-diphenylethylamine hydrochloride and methyl (±)-phenylglycinate hydrochloride in enantiomer differential transport has been examined. The enantiomer selectivities of these crown ethers in complexation with racemic ammonium salts have been interpreted on the basis of CPK molecular model examination of the diastereoisomeric complexes.