Easy kinetic resolution of some bêta-amino alcohols by Candida antarctica lipase B catalyzed hydrolysis in organic media
Herein, we present an easy and eco-friendly pathway to obtain some enantiomerically enriched b-amino alcohols using essentially as b-blockers. The enzymatic hydrolysis is conducted in hydrophobic organicmedia, assisted by sodium carbonate and CAL-B. We describe a new and effective procedure in terms...
| Published in: | Tetrahedron: Asymmetry |
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| Main Authors: | , , , |
| Other Authors: | |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
Pergamon
2016
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| Subjects: | |
| Online Access: | http://hdl.handle.net/2078.1/181204 https://doi.org/10.1016/j.tetasy.2016.10.003 |
| Summary: | Herein, we present an easy and eco-friendly pathway to obtain some enantiomerically enriched b-amino alcohols using essentially as b-blockers. The enzymatic hydrolysis is conducted in hydrophobic organicmedia, assisted by sodium carbonate and CAL-B. We describe a new and effective procedure in terms of the chemo- and enantioselectivity, which allows for the formation of both enantiomers: the 2-acetamido-1-arylacetates and 2-acetamido-1-arylethanols were obtained with high ee values (up to >99%), while the selectivities reached E >200. The obtained results show a high CAL-B affinity toward the deacylation of the 2-acetamido-1-arylacetates compared to the acylation one. The structure of the 2-acetamido-1-arylacetates had a significant influence on both reactivity and selectivity of the CAL-B catalyzed deacylation. A multigram scale O-deacylation of racemic 2-acetamido-1-phenylacetate has been carried out, giving access both enantiomers with high enantiomeric purity and good isolated chemical yields. |
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