Liquid chromatographic resolution of biphenyl dimethyl dicarboxylate (DDB) and its analogues on a chiral stationary phase.
Racemic biphenyl dimethyl dicarboxylate (DDB) and its analogues have been successfully resolved on a commercial HPLC chiral column, (3R,4S)-Whelk-O 1. In general, cyclic amide analogues of DDB, which were derived from pyrrolidine or piperidine, showed greater enantioselectivity and greater retention than the corresponding N,N-dialkyl amide or N-alkyl amide or ester analogues. From these results, it was concluded that the carbonyl oxygen of the DDB analogues plays an important role as a hydrogen bond acceptor, though the steric bulkiness of the amide functionality of DDB analogues may be another factor governing chiral recognition. The conformational stability of the two enantiomers of DDB and its analogues was also found to be high enough for the two enantiomers to be resolvable on (3R,4S)-Whelk-O 1.
Hyun
M H
MH
Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Republic of Korea. mhhyun@hyowon.pusan.ac.kr
Lee
G S
GS
Han
S C
SC
Cho
Y J
YJ