Abstract
Two lipases, Novozyme 435 (lipase B from Candida Antarctica) and Lipozyme TL IM (Thermomyces lanuginosus) were used successfully for the kinetic resolution of racemic 1-(2-furyl)-3-pentanol, the key intermediate in synthesis of the bark beetle pheromone, chalcogran. The desired S-(+)-enantiomer was prepared in enantiomeric excesses higher than 98 % and with yields of 26.3 % and 32.5 %, respectively. Methyl tert-butyl ether and vinyl acetate were found to be the best reaction media and the acetyl donor to achieve fast and effective resolution.
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Mastihuba, V., Čepec, P., Vlčková, S. et al. Enzymatic synthesis of a chiral chalcogran intermediate. Chem. Pap. 68, 745–750 (2014). https://doi.org/10.2478/s11696-013-0523-5
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DOI: https://doi.org/10.2478/s11696-013-0523-5