Gold(I)-Catalyzed Oxidative 1,4-Additions of 3-En-1-ynamide with Nitrones via Carbon- versus Nitrogen-Addition Chemoselectivity.

This work reports gold-catalyzed 1,4-oxofunctionalizations of 3-en-1-ynamides with nitrones, yielding two distinct -configured products. We obtained 1,4-oxoarylation products from 3-en-1-ynamides bearing C(4)-electron-donating substituents and 1,4-oxoamination products from those analogues bearing C(4)-aryl substituents. We propose that if vinylgold carbenes are stable, imines undergo a -arylation on these gold carbenes.