RESOLUTION OF 2-METHYLALKANOIC ESTERS - ENANTIOSELECTIVE AMINOLYSIS BY (R)-1-PHENYLETHYLAMINE OF ETHYL 2-METHYLOCTANOATE CATALYZED BY LIPASE-B FROM CANDIDA-ANTARCTICA

Authors
VORDE C HOGBERG HE HEDENSTROM E
Citation
C. Vorde et al., RESOLUTION OF 2-METHYLALKANOIC ESTERS - ENANTIOSELECTIVE AMINOLYSIS BY (R)-1-PHENYLETHYLAMINE OF ETHYL 2-METHYLOCTANOATE CATALYZED BY LIPASE-B FROM CANDIDA-ANTARCTICA, Tetrahedron : asymmetry, 7(5), 1996, pp. 1507-1513
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
5
Year of publication
1996
Pages
1507 - 1513
Database
ISI
SICI code
0957-4166(1996)7:5<1507:RO2E-E>2.0.ZU;2-E
Abstract
Enantiomerically pure (R)-1-phenylethylamine and ethyl rac-2-methyloct anoate in the presence of lipase from Candidada antarctica (Novozym 43 5) reacted to give (R)-2-methyloctanoic (R)-1-phenylethylamide as the predominant diastereomer of 30 - 40% de at approximate to 100% convers ion. 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 alpha-carbon o f the acyl moiety under the reaction conditions. The diastereomeric am ides were obtained pure after liquid chromatography. Copyright (C) 199 6 Elsevier Science Ltd