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Preparation and lipase catalyzed O-acetylation of ferrocene alcohols

The development of new synthetic methods for the preparation of non-racemic chiral ferrocenes is an important goal in view of the use of these compounds as ligands in asymmetric synthesis [1]. Ferrocenyl derivatives bearing a stereocenter in beta-position of the side chain have received much less attention due to the lack of suitable homochiral starting materials [2]. In continuation of our research on biocatalyzed acylations of ferrocene carbinols [3], secondary beta-ferrocenylalkanols 1-3, as well as the corresponding acetates 4-6 were synthesized. The alcohols prepared were submitted to enantioselective biotransesterifications modifying several reaction parameters (temperature, solvent, acyl donor and microbial lipases) and monitored their effect on these biotransformations. The course of the conversions was followed by HPLC technique and the optical purity of the compounds prepared was examined on the chiral columns.

ferrocene alcohols; lipase; enantioselectivity

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