Gold-Catalyzed, SN1-Type Reaction of Alcohols to Afford Ethers and Cbz-Protected Amines

The use of a gold-catalyzed, microwave protocol to activate alcohols through an intermolecular, S(N)1-type reaction to directly form unsymmetrical ethers and N-benzyloxy carbamate- (Cbz) protected amines is reported. Results have shown this reaction to be highly reproducible and tolerant of moisture, and moderate to high product yields (53-99%) were obtained. Significantly, the intermolecular catalytic amination of alcohols to directly afford Cbz-protected amines is heretofore unprecedented using gold catalysis.