BIOCATALYTIC RESOLUTIONS OF SULFINYLALKANOATES - A FACILE ROUTE TO OPTICALLY-ACTIVE SULFOXIDES

Two methods are presented for kinetic resolutions of compounds containing ester and sulfoxide functionalities (sulfinylalkanoates). In the first a crude lipase preparation from Pseudomonas sp. (K10) mediates enantioselective hydrolysis of these esters in an aqueous environment. The second method uses the same lipase preparation to promote enantioselective transesterifications with alcohols in hexane. Both procedures are suitable for preparation of sulfinylalkanoates where the ester and sulfoxide groups are separated by one or two methylene units (sulfinylacetates and sulfinylpropanoates) but compounds with three methylene "spacer groups" (sulfinylbutanoates) are not substrates for the lipase under either set of conditions.