S-ethyl thiooctanoate as acyl donor in lipase catalysed resolution of secondary alcohols

✍ Scribed by Hans Frykman; Niklas Öhrner; Torbjörn Norin; Karl Hult

• Publisher: Elsevier Science
• Year: 1993
• Tongue: French
• Weight: 226 KB
• Volume: 34
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)91797-0

✦ Synopsis

The use of S-ethyl du 'oo&moate as acyl donor in resolution of secondary alcohols by lipase catalysed transeskfkation, resulted in an efficient displacement of rhe equilibrium towards esterification of the alcohol. A lii (component B) from Can&a antarctica was used 89 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. I-phenyl e&anol, l-cyclohexyl ethanol and rrans-Zmethyl cyclohexanol were also resolved with good optical yields. After 50% conversion on a preparative scale, 15 g of alcohol, the (S)enantiomer of 2-ectaaol could be obtained with aa eoantiomaic excess of %%. The (R)cnantiomer was isolated with aa enaotiomeric excess of 97% after hydrolysis of the produced eater.