‘Gelozymes’ in organic synthesis. (Part 3): Lipase mediated synthesis of enantiomerically pure (R)- and (S)-enantiomers of 2-acetoxy-4-phenyl-(E)-but-3-enenitrile

Add time:08/05/2019    Source:sciencedirect.com

Lipases such as Candida rugosa lipase and Pseudomonas cepacia (Amano Ps) lipase immobilized in gelatin gels (gelozymes) exhibit very high enantioselectivities (E>200) during alcoholysis of racemic 2-acetoxy-4-phenyl-(E)-but-3-enenitrile with n-butanol in hexane and diisopropyl ether. C. rugosa lipase in n-hexane shows selectivity towards the (R)-ester while P. cepacia (Amano Ps) lipase shows selectivity towards the (S)-ester producing the corresponding cyanohydrins. After decomposition of the cyanohydrin by treatment with 1 M imidazole solution to cinnamaldehyde and its removal by bisulfite treatment, (R)- or (S)-enantiomer of 2-acetoxy-4-phenyl-(E)-but-3-enenitrile can be obtained in high yields (90%) and high enantiomeric excess (>99%).

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