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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
Author(s) -
Taji Hiromi,
Kasai Yusuke,
Sugio Akinori,
Kuwahara Shunsuke,
Watanabe Masataka,
Harada Nobuyuki,
Ichikawa Akio
Publication year - 2001
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10038
Subject(s) - enantiopure drug , chemistry , diastereomer , hydrolysis , anisotropy , elution , chromatography , chiral derivatizing agent , absolute configuration , organic chemistry , high performance liquid chromatography , chiral column chromatography , catalysis , enantioselective synthesis , physics , quantum mechanics
The enantioresolution of racemic alcohols as esters of 2‐methoxy‐2‐(1‐naphthyl)propionic acid (MαNP acid 1 ) and the determination of their absolute configurations on the basis of 1 H NMR anisotropy effect are described. The enantiopure MαNP 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. Chirality 14:81–84, 2002. © 2002 Wiley‐Liss, Inc.