Tetrahedron Letters p. 1367 - 1370 (1993)
Update date:2022-08-10
Topics:
Frykman
Ohrner
Norin
Hult
The use of S-ethyl thiooctanoate as acyl donor in resolution of secondary alcohols by lipase catalysed transesterification, resulted in an efficient displacement of the equilibrium towards esterification of the alcohol. A lipase (component B) from Candida antarctica was used as the catalyst. On a semi-preparative scale, 0.5 g of 2-octanol was resolved in less than one hour, affording an enantiomeric excess of >98% of the remaining alcohol and >97% of the produced ester. Three other alcohols, 1-phenyl ethanol, 1-cyclohexyl ethanol and trans-2-methyl cyclohexanol were also resolved with good optical yields. After 50% conversion on a preparative scale, 15 g of alcohol, the (S)-enantiomer of 2-octanol could be obtained with an enantiomeric excess of 96%. The (R)-enantiomer was isolated with an enantiomeric excess of 97% after hydrolysis of the produced ester.
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