Enzyme-promoted kinetic resolution of acetoxymethyl aryl sulfoxides

• The first enzymatic synthesis of optically active acetoxymethyl aryl sulfoxides.
• The hydrolysis was achieved in organic solvents without the external water added.
• The enzymatic approach proved superior to chemical methods.

A simple and efficient method of the synthesis of enantiomerically enriched, unknown acetoxymethyl aryl sulfoxides has been developed which is based on an enzyme-catalyzed hydrolysis of racemic substrates under the kinetic resolution conditions. The hydrolysis was performed not only in a buffer solution but also in diisopropyl ether in the absence of the external water added to give in some cases the products with ee up to 98%. The enantioselectivity of both procedures was dependent on the enzyme used and the aryl substituent, being lower for p-tolyl than for phenyl. A comparative asymmetric synthesis based on the oxidation of the corresponding sulfides using chiral oxidizing reagent turned out to be inferior to the method described. Absolute configuration of the newly synthesized compounds was ascribed on the basis of CD spectra.

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