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- W2897587177 abstract "Abstract 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 Na 2 CO 3 in organic media under mild conditions. The reaction parameters solvent effect, amount of lipase, and Na 2 CO 3 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 NEt 3 . 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." @default.
- W2897587177 created "2018-10-26" @default.
- W2897587177 creator A5053302158 @default.
- W2897587177 creator A5078242156 @default.
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- W2897587177 date "2018-10-08" @default.
- W2897587177 modified "2023-09-30" @default.
- W2897587177 title "Efficient access to both enantiomers of 3-(1-hydroxyethyl)phenol by regioselective and enantioselective <i>CAL-B</i> -catalyzed hydrolysis of diacetate in organic media by sodium carbonate" @default.
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- W2897587177 doi "https://doi.org/10.1002/chir.23025" @default.
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