Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1209450 | Journal of Chromatography A | 2006 | 9 Pages |
Abstract
To investigate the resolution of secondary alcohols using 2-methoxy-2-(1-naphthyl)propionic acid (MαNP acid), 2-methyl-4-heptanol, one of the aggregation pheromones of Metamasius hemipterus, was resolved using (S)-MαNP acid. As a chiral-resolving agent, MαNP acid is superior to 3,3,3-trifluoro-2-methoxy-2-phenylpropionic acid (MTPA) in terms of HPLC separation and NMR shielding. A better separation of diastereomeric MαNP esters was observed when n-hexane-THF was used as the eluent for silica gel HPLC. The solvolysis of the diastereomeric MαNP esters gave (R)-2-methyl-4-heptanol and its enantiomer; enantiopure (S)-MαNP acid was also recovered. In addition, the preferred conformation of the MαNP ester was confirmed using methyl (R)-3-hydroxyvalerate as an authentic compound.
Keywords
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Physical Sciences and Engineering
Chemistry
Analytical Chemistry
Authors
Akio Ichikawa, Hiroshi Ono,