title: The effects of aromatic substituents on the chromatographic enantioseparation of diarylmethyl esters with the whelk-O1 chiral stationary phase.
abstract: 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.
authors.affiliation: School of Chemical Sciences, University of Illinois, Urbana, IL 61801, USA. gejob@mit.edu
authors.forename: Gabriel E
authors.initials: GE
authors.lastname: Job
authors.forename: Alex
authors.initials: A
authors.lastname: Shvets
authors.forename: William H
authors.initials: WH
authors.lastname: Pirkle
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Kuwahara
authors.forename: Masashi
authors.initials: M
authors.lastname: Kosaka
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Kasai
authors.forename: Hiromi
authors.initials: H
authors.lastname: Taji
authors.forename: Kaori
authors.initials: K
authors.lastname: Fujita
authors.forename: Masataka
authors.initials: M
authors.lastname: Watanabe
authors.forename: Nobuyuki
authors.initials: N
authors.lastname: Harada
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation*; D004952:Esters / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
chemical_list: D004952:Esters