Nm. Carballeira et R. Colon, The use of (S)-(-)-1-(1-naphthyl)ethylamine as a resolving agent for alpha-methoxy fatty acids, TETRAHEDR-A, 10(19), 1999, pp. 3785-3790
A general method was developed for the diastereoselective resolution of alp
ha-methoxy fatty acids utilizing (S)(-)-1-(1-naphthyl)ethylamine as resolvi
ng agent. The diastereomeric amides can be easily separated by silica gel c
olumn chromatography and/or capillary gas chromatography, thus allowing for
a preparative and analytical method for determining the enantiomeric purit
y of naturally occurring and/or synthetic alpha-methoxy fatty acids. The fi
rst synthesis of the naturally occurring (R)-2-methoxyhexadecanoic acid was
also accomplished in four steps starting from commercially available (+/-)
-2-hydroxyhexadecanoic acid. (C) 1999 Elsevier Science Ltd. All rights rese
rved.