Efficient access to both enantiomers of 3-(1-hydroxyethyl)phenol by regioselective and enantioselective CAL-B -catalyzed hydrolysis of diacetate in organic media by sodium carbonate
| Autor: | Nabila Braia, Louisa Aribi-Zouioueche, Mounia Merabet-Khelassi |
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| Rok vydání: | 2018 |
| Předmět: |
Pharmacology
biology 010405 organic chemistry Chemistry Phenyl acetate Organic Chemistry Alkaline hydrolysis (body disposal) 010402 general chemistry biology.organism_classification 01 natural sciences Catalysis 0104 chemical sciences Analytical Chemistry Acylation chemistry.chemical_compound Hydrolysis Drug Discovery biology.protein Vinyl acetate Phenol Organic chemistry Candida antarctica Lipase Spectroscopy |
| Zdroj: | Chirality. 30:1312-1320 |
| ISSN: | 0899-0042 |
| DOI: | 10.1002/chir.23025 |
| Popis: | In the present paper, we describe several pathways employing immobilized lipase from Candida antarctica B (CAL-B) as biocatalyst to prepare easily both enantiomers of 3-(1-hydroxyethyl)phenol. We have applied hydrolysis with Na2 CO3 in organic media under mild conditions. The reaction parameters solvent effect, amount of lipase, and Na2 CO3 were examined with 3-(1-acetoxyethyl)phenyl acetate as substrate. In alkaline hydrolysis, (R)-3-(1-hydroxyethyl)phenol was obtained with ee = 99% and (S)-(-)-3-(1-acetoxyethyl)phenol with ee = 98% at optimal conversion (c = 50%) and high selectivity (E > 200). Two other deacylation reactions were compared: alcoholysis with MeOH and with NEt3 . The acylation of 3-(1-hydroxyethyl)phenol with vinyl acetate was also examined. Alkaline hydrolysis gave the best results, while good regioselectivity and enantioselectivity were observed in alcoholysis and acylation reactions. Finally, (S)- and (R)-3-(1-hydroxyethyl)phenol (ee > 98%), key intermediates for the synthesis of important drugs, were prepared from the corresponding racemic diacetate through alkaline hydrolysis. |
| Databáze: | OpenAIRE |
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