TY - JOUR
T1 - 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
AU - Naemura, Koichiro
AU - Miyabe, Hajime
AU - Shingai, Yasuhiro
AU - Tobe, Yoshito
PY - 1993/12/1
Y1 - 1993/12/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=37049075446&partnerID=8YFLogxK
U2 - 10.1039/p19930001073
DO - 10.1039/p19930001073
M3 - Article
AN - SCOPUS:37049075446
SP - 1073
EP - 1077
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
SN - 0300-922X
IS - 9
ER -