Palladium-Catalyzed Addition of 1,3-Diones to Ynamides: An Entry to Alkoxy-Substituted Enamides
Résumé
A new metal-catalyzed addition reaction of 1,3-diketones to ynamides, which provides access to unprecedented alkoxy- substituted enamides, is disclosed herein. A screening of cata- lytic systems showed that both a phosphapalladacycle and a cationic gold complex were capable of promoting this reac- tion rapidly and cleanly. The scope investigation revealed that variously substituted terminal ynamides and cyclic 1,3-diones were well tolerated. The use of internal ynamides led to the formation of both E and Z isomers with low to good selectivi- ties. The proposed mechanism suggests that the phosphapalla- dacycle acts as a p Lewis acid to activate the ynamide.
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