Gold(I)-catalyzed, stereocontrolled enamide synthesis from primary amides and propargyl aldehydes using a tandem strategy

Abstract

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.