engleski

Lipase Catalyzed Stereoselective Acylation of Ferrocene Aliphatic and Aromatic Diols

The aim of the work presented was a study of stereoselectivity in biocatalyzed acylation of some ferrocene diols depending on lenght of the containing aliphatic chain or aromatic ring substituted with hydroxy functions. With this intention a series of racemic ferrocene aliphatic (1-5) and aromatic diols (6-8) were prepared by reduction of the corresponding keto esters. Each of these diols contains one secondary and one primary carbinol group, separated by 1-5 methylene units or by benzene ring. The carbinols prepared underwent stereoselective acylation in benzene at 27 °C by the action of vinyl acetate as acyl group donor in the presence of various lipases giving the corresponding acetates (9-16). The course of these conversions was followed by the HPLC technique and the optical purity of the compounds prepared was examined on a chiral column Chiracel OD-H and Chiracel OJ.

ferrocene aliphatic and aromatic diols; stereoselective acylation; optical purity; chiral columns

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