The Development of New Gold-Catalyzed Reactions Using a Tandem Strategy

Abstract

Recently, tandem reactions have been issued in organic synthesis area due to its step-economical advantage. A novel strategy for enamide synthesis from primary amides and propargyl aldehydes via Au(I)-catalyzed tandem amide addition and Meyer-Schuster rearrangement is described. In situ generated hemiaminals were successfully converted to the desired products under the optimized conditions. Enamide stereochemistry was controlled simply by changing solvents and adding a catalytic amount of acid. The developed synthetic strategy provides a new method to synthesize various β-substituted-α,β-unsaturated carbonyl compounds.