Baeyer-Villiger monooxygenase-catalyzed desymmetrizations of cyclobutanones. Application to the synthesis of valuable spirolactones
| Autor: | Vicente Gotor, Javier Mendiola, Ivan Collado, Oscar de Frutos, Susana García-Cerrada, Vicente Gotor-Fernández, Iván Lavandera, María Rodríguez-Mata |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Chemistry Organic Chemistry Enantioselective synthesis Side reaction Alcohol Monooxygenase 010402 general chemistry 01 natural sciences Biochemistry Desymmetrization 0104 chemical sciences Catalysis Baeyer–Villiger oxidation chemistry.chemical_compound Drug Discovery Organic chemistry Enantiomeric excess |
| Zdroj: | Scopus RUO. Repositorio Institucional de la Universidad de Oviedo instname |
| Popis: | A series of γ-butyrolactone derivatives, including some spiranic ones, was obtained through desymmetrization of the corresponding prochiral 3-substituted cyclobutanones via Baeyer–Villiger monooxygenase (BVMO)-catalyzed oxidation. After reaction optimization using several commercial enzymes, both antipodes of various lactones were synthesized in most cases with >90% conversion and >80% enantiomeric excess under mild reaction conditions. In some cases alcohol formation was also observed (up to 40% conversion) as an undesired side reaction due to the presence of alcohol dehydrogenases in these preparations. Selected transformations were achieved on a 100 mg scale showing the possibilities of these oxidative biocatalysts as a new source of highly interesting compounds. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|