Resolution of 2-methylalkanoic esters: Enantioselective aminolysis by (R)-1-phenylethylamine of ethyl 2-methyloctanoate catalysed by lipase B from Candida antarctica

✍ Scribed by Carin Vörde; Hans-Erik Högberg; Erik Hedenström

• Publisher: Elsevier Science
• Year: 1996
• Tongue: English
• Weight: 448 KB
• Volume: 7
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/0957-4166(96)00170-x

✦ Synopsis

Enantiomerically pure (R)-l-phenylethylamine and ethyl rac-2methyloctanoate in the presence of lipase from Candidada antarctica (Novozym 435) reacted to give (R)-2-methyloctanoic (R)-l-phenylethylamide as the predominant diastereomer of 30 -40% de at = 100% conversion. Ethyl rac-2-methyldecanoate and ethyl rac-2-methylhexanoate gave similar results. The diastereomeric excess was almost constant from 0% -100% conversion probably due to epimerisation of the c~carbon of the acyl moiety under the reaction conditions. The diastereomeric amides were obtained pure after liquid chromatography.