Research Projects

α-Oxycarbonyls are essential for the synthesis of natural products, pharmaceuticals, and bioactive molecules. C-O cleavage/oxirane ring opening is the primary method for transforming these compounds, but it has disadvantages such as toxic reagents, harsh reaction conditions, poor yields, and selectivity. Typically, epoxy ketone, carboxylic acid, ester, and amide derivatives participate in these C-O bond cleavage reactions under reducing conditions. However, the reductive C-O cleavage of epoxyaldehyde is accompanied by unwanted oxidative modification, preventing uninterrupted synthetic elaborations of desired β-hydroxyaldehyde functionality. The synthesis of enantioenriched amino alcohols is tedious and often requires harsh reductive C-O bond cleavage steps, which limits the use of sensitive substrates like epoxyaldehyde. To address these issues, an unprecedented method of aminative C-O cleavage of α-oxyketone and α-oxyaldehyde is proposed. This method works under metal-free mild conditions, making it applicable to sensitive substrates like α-oxyaldehyde. The reaction provides β-hydroxy ketone/aldehyde and 1,3-aminoalcohols via hydrolysis and reduction of imino diene. The developed methodology will be applied for the efficient asymmetric synthesis of aminoalcohol-based antidepressant drugs duloxetine and atomoxetine.