The effects of aromatic substituents on the chromatographic enantioseparation of diarylmethyl esters with the whelk-O1 chiral stationary phase.
Members of a series of diarylmethanols, diarylmethyl pivalates, and diarylmethyl acetates (analyte sets 1-26) were enantioresolved with the (S,S)-Whelk-O1 chiral stationary phase (CSP). An analogue of the (S,S)-Whelk-O1 selector was combined with enantioenriched samples of the various diarylmethyl pivalates and thereby used as a chiral solvating agent (CSA) for high field 1H NMR studies. The absolute configurations of a number of chiral diarylmethyl pivalates were assigned using this approach, and hydrolysis of the pivalates allowed assignment of the absolute configurations of the corresponding diarylmethanols. Chromatographic, 1H NMR, and X-ray evidence are given in support of a chiral recognition model for the enantioresolution of diarylmethyl esters on this CSP.
Job
Gabriel E
GE
School of Chemical Sciences, University of Illinois, Urbana, IL 61801, USA. gejob@mit.edu
Shvets
Alex
A
Pirkle
William H
WH
Kuwahara
Shunsuke
S
Kosaka
Masashi
M
Kasai
Yusuke
Y
Taji
Hiromi
H
Fujita
Kaori
K
Watanabe
Masataka
M
Harada
Nobuyuki
N
D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation*; D004952:Esters / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D004952:Esters