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Enzymes represent attractive catalysts for sustainable synthesis given their ability to perform under mild conditions and carry out highly selective transformations. However, their adoption in industry is hampered by the limited scope of enzymatic reactions available. We seek to overcome this limitation by exploring the use of thiamine-dependent enzymes for synthesis of α-substituted ketones, which are precursors to more complex, bioactive compounds. This will be accomplished by screening enzymes against substrates possessing multiple chiral centers to form stereochemically complex products. This research will expand the scope of reactions available to thiamine-dependent enzymes, making them more broadly useful for chemical synthesis.