Practical enantioresolution of alcohols with 2‐methoxy‐2‐(1‐naphthyl)propionic acid and determination of their absolute configurations by the 1H NMR anisotropy method
- 11 December 2001
- Vol. 14 (1) , 81-84
- https://doi.org/10.1002/chir.10038
Abstract
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 1H 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 1H NMR anisotropy method, the general scheme was proposed. Separated esters were reduced with LiAlH4 or hydrolyzed with KOH/EtOH to recover enantiopure alcohols. Chirality 14:81–84, 2002.Keywords
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