Resolution of 2-methylalkanoic esters: Enantioselective aminolysis by (R)-1-phenylethylamine of ethyl 2-methyloctanoate catalysed by lipase B from Candida antarctica
| Autor: | Carin Vörde, Hans-Erik Högberg, Erik Hedenström |
|---|---|
| Rok vydání: | 1996 |
| Předmět: |
biology
Resolution (mass spectrometry) Chemistry Organic Chemistry Enantioselective synthesis Diastereomer biology.organism_classification Catalysis Inorganic Chemistry chemistry.chemical_compound Aminolysis 1-Phenylethylamine biology.protein Moiety Organic chemistry Candida antarctica Physical and Theoretical Chemistry Lipase |
| Zdroj: | Tetrahedron: Asymmetry. 7:1507-1513 |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/0957-4166(96)00170-x |
| Popis: | Enantiomerically pure ( R )-1-phenylethylamine and ethyl rac -2-methyloctanoate in the presence of lipase from Candidada antarctica (Novozym 435) reacted to give ( R )-2-methyloctanoic ( R )-1-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 α-carbon of the acyl moiety under the reaction conditions. The diastereomeric amides were obtained pure after liquid chromatography. |
| Databáze: | OpenAIRE |
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