Enantiomerically enriched cryptone by lipase catalysed kinetic resolution
| Autor: | Dan Isaksson, Kristina Sjödin, Hans-Erik Högberg |
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| Rok vydání: | 2006 |
| Předmět: |
biology
Chemistry organic chemicals Thiophenol Organic Chemistry Cyclohexanone Alcohol biology.organism_classification Catalysis Kinetic resolution Inorganic Chemistry Acylation chemistry.chemical_compound biology.protein Organic chemistry Candida antarctica Physical and Theoretical Chemistry Lipase Enantiomer |
| Zdroj: | Tetrahedron: Asymmetry. 17:275-280 |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/j.tetasy.2005.12.012 |
| Popis: | Thiophenol was added to racemic cryptone (4-isopropyl-2-cyclohexene-1-one) and the resulting 1,4-addition products, cis- and trans-4-isopropyl-3-(phenylsulfanyl)cyclohexanone) were separated and the latter reduced to rac-1,3-cis-1,4-trans-4-isopropyl-3-(phenylsulfanyl)cyclo¬he¬xanol which was subjected to lipase catalysed resolution by acylation catalysed by CAL-B (Candida antarctica lipase B). The remaining alcohol was separated from the produced acetate, which was hydrolysed to the alcohol. The enantiomeric alcohols so obtained were oxidised. The initial products, probably sulfoxidoketones spontaneously decomposed to furnish enantiomerically enriched (R)- and (S)-cryptone with up to 76% and 98% ee, respectively. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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