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. |
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| Authors: | Hiromi Taji Yusuke Kasai Akinori Sugio Shunsuke Kuwahara Masataka Watanabe Nobuyuki Harada Akio Ichikawa |
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| Institution: | Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1 Katahara, Aoba, Sendai 980-8577, Japan. |
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| 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. |
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| Keywords: | racemic 2‐alkanols 1‐octyn‐3‐ol diastereomeric mixtures HPLC separation on silica gel enantiopure alcohols |
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