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Synthesis of Amide Enol Carbamates and Carbonates through Cu(OTf)2-Catalyzed Reaction of Ynamides with t-Butyl Carbamates/Carbonates.

A highly regioselective approach to access amide enol carbamates and carbonates 5a-5c', 7a-7h and 9 was developed through Cu(OTf)2 catalyzed reactions of ynamides 4 with t-butyl carbamates 2, 8 and t-butyl carbonates 6. Moreover, this strategy was successfully applied to generate amide enol carbamates 11a-11s and 14a-14f from imide 10 and 13 with ynamides through a N-Boc cleavage-addition-ring opening process. A range of substituents were amenable to this transformation and the desired amide enol carbamates and carbonates were obtained in moderate to good yields.