Activation of carbon-oxygen bonds by palladium: toward a mild, catalytic approach to alpha-amino acid derivatives

A Lewis acid mediated method to induce the carbon-oxygen bond of amide-substituted ethers to undergo addition to palladium is described. The product of this reaction has been crystallographically characterized. This reaction suggests the potential use of such ethers as an alternative to organic halides in palladium catalyzed carbon-carbon bond formation. As an illustration of this potential, this reaction has been used to design a mild, catalytic route to alpha-amino acid derivatives from alpha-phenoxyamides and carbon monoxide.