Enzyme-catalyzed addition of diazo compounds to in-situ generated imines

Abstract

The nucleophilic addition of diazo compounds with imines is known for a long time. While a number of bases, organocatalysts, etc., have been used to catalyze this reaction no enzyme is explored so far. Herein, we report a biocatalytic nucleophilic addition of diazo compounds with in-situ generated imines by the reaction between 2-amino pyridine and benzaldehyde using an α-amylase enzyme under sustainable reaction conditions. To prove the generality of this transformation differently substituted 2-amino pyridines, benzaldehydes along with ethyl diazoacetate were tested, and afforded the corresponding products in moderate to good yields. Moreover, control experiments are performed those suggest that the reaction might be getting catalyzed in the natural active-site of the α-amylase enzyme.