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

Kou Hiroya; Jin Hasegawa; Takashi Watanabe; Kunio Ogasawara

doi:10.1055/s-1995-3931

Synthesis 1995; 1995(4): 379-381
DOI: 10.1055/s-1995-3931

short paper

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

Kou Hiroya, Jin Hasegawa, Takashi Watanabe, Kunio Ogasawara^*

^*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-77, Japan, Fax +81(22)2681541

Abstract

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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.

kinetic diastereoselective separation - lipase-mediated diastereoselective separation - 4-tert-butylcyclohexanemethanol - kinetic acylation - kinetic hydrolysis

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