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3(RS)-Hydroxy-2-methylenebutanenitrile was synthesized from acetaldehyde and acrylonitrile with DABCO as a catalyst. Optimization of the reaction conditions was conducted because some literature procedures were not reproducible. Asymmetric transesterification of the Morita-Baylis-Hillman adduct was carried out using ten lipases. The hydroxyl-nitrile was also esterified chemically and subjected to enzymatic hydrolysis with the same set of enzymes. The best results were obtained with lipase from Candida antarctica and Novozyme 435. The absolute configuration of an optically pure hydroxyl-nitrile was determined by Mosher’s method.

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Synthesis, lipase catalyzed kinetic resolution, and determination of the absolute configuration of enantiomers of the Morita-Baylis-Hillman adduct 3-hydroxy-2-methylenebutanenitrile