Collect. Czech. Chem. Commun. 1998, 63, 525-533

Enantioselective Preparation of the Stereoisomersof 4-Methylheptan-3-ol Using Candida antarctica Lipase B

C. Rikard Unelius, Johan Sandell and Christian Orrenius

Department of Chemistry, Organic Chemistry, Royal Institute of Technology, SE-100 44 Stockholm, Sweden


The four stereoisomers of 4-methylheptan-3-ol were prepared through fractional crystallization of a mixture of their racemic 4-methylhept-3-yl 3,5-dinitrobenzoates, followed by hydrolysis of each crystalline racemate and enantioselective, lipase-mediated transesterification of each pair of enantiomeric alcohols liberated, using the Candida antarctica lipase B as catalyst and S-ethyl octanethioate as the acyl donor. An analytical method of determining the enantiomeric composition of mixtures of 4-methyl-heptan-3-ols was developed. The optical purity of the separated isomers was in the range of 29-97%.

Keywords: 4-Methylheptan-3-ol; Candida antarctica lipase B; Enzymatic resolution.