title: Practical enantioresolution of alcohols with 2-methoxy-2-(1-naphthyl)propionic acid and determination of their absolute configurations by the (1)H NMR anisotropy method.
abstract: The enantioresolution of racemic alcohols as esters of 2-methoxy-2-(1-naphthyl)propionic acid (MalphaNP acid 1) and the determination of their absolute configurations on the basis of (1)H NMR anisotropy effect are described. The enantiopure MalphaNP acid (S)-(+)-1 was allowed to react with racemic 2-alkanols and 1-octyn-3-ol, yielding diastereomeric mixtures of esters, which were easily separated by HPLC on silica gel. To determine the absolute configurations of the first-eluted diastereomeric esters by the (1)H NMR anisotropy method, the general scheme was proposed. Separated esters were reduced with LiAlH(4) or hydrolyzed with KOH/EtOH to recover enantiopure alcohols.
authors.affiliation: Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1 Katahara, Aoba, Sendai 980-8577, Japan.
authors.forename: Hiromi
authors.initials: H
authors.lastname: Taji
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Kasai
authors.forename: Akinori
authors.initials: A
authors.lastname: Sugio
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Kuwahara
authors.forename: Masataka
authors.initials: M
authors.lastname: Watanabe
authors.forename: Nobuyuki
authors.initials: N
authors.lastname: Harada
authors.forename: Akio
authors.initials: A
authors.lastname: Ichikawa