American Chemical Society
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Gold(I)-Catalyzed, Stereocontrolled Enamide Synthesis from Primary Amides and Propargyl Aldehydes Using a Tandem Strategy

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journal contribution
posted on 2014-12-05, 00:00 authored by Sang Min Kim, Dabon Lee, Soon Hyeok Hong
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.