Lipase-Mediated Kinetic Separation of a Diastereomeric Mixture of 4-tert-Butylcyclohexanemethanol

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Abstract
Diastereomerically pure trans- and cis-4-tert-butylcylcohexanemethanols have been obtained by kinetic acylation of the diastereomeric alcohol in an organic medium and by kinetic deacylation of the diastereomeric acetate in an aqueous medium both in the presence of the same lipase (lipase PS, Pseudomonas sp., Amano). The reactions take place preferentially with the trans-isomers both in organic and aqueous media to give the trans-acetate with recovery of the cis-alcohol on acylation in an organic medium, and the trans-alcohol with recovery of the cis-acetate on deacylation in an aqueous medium.

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