Studies towards dynamic kinetic resolution of 4-hydroxy-2-methylcyclopent-2-en-1-one and its E - O -trityloxime
| Autor: | Karol Michalak, Jerzy Wicha, Jacek Wójcik |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
biology
010405 organic chemistry Chemistry Stereochemistry Organic Chemistry 010402 general chemistry biology.organism_classification 01 natural sciences Biochemistry Redox 0104 chemical sciences Kinetic resolution Catalysis Metal Intramolecular force visual_art Drug Discovery biology.protein visual_art.visual_art_medium Candida antarctica Lipase Racemization |
| Zdroj: | Tetrahedron. 72:4813-4820 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2016.06.047 |
| Popis: | Dynamic kinetic resolution through metal complex induced racemization and Candida antarctica lipase mediated enantioselective acetylation of a model hydroxy-ketone: 4-hydroxy-2-methylcyclopent-2-en-1-one and its selected derivatives, has been studied. Racemization of the hydroxy-ketone was efficiently affected by [RuCl2(cymene)]2 complex–triethylamine while Shvo's catalyst triggered an intramolecular redox process. Kinetic resolution of 4-hydroxy-2-methylcyclopent-2-en-1-one with C. antarctica under conditions compatible with [RuCl2(cymene)]2 racemization failed to reach the efficiency threshold. However, dynamic kinetic resolution of its O-trityloxime using [RuCl2(cymene)]2–triethylamine and C. antarctica lipase–isopropenyl acetate combination, was successfully achieved. |
| Databáze: | OpenAIRE |
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