ether motif gave slightly better yields than electron rich rings (5e vs 5j), whereas the alkyl-DHP had negligible effect on the outcome (5h vs 5i). C(sp 2 )-I bonds are prone to react under photocatalytic conditions, and we were pleased that 5g could be isolated in moderate yield. Complete (Z)-selectivity was retained in the furnished enol ethers. A range of (Z)-N-VBX reagents were then reacted with 1r to give the corresponding trisubstituted enamides 5k-5n with retained (Z)-configuration. To further evaluate the scope of the vinylation, we investigated whether a glycosyl radical could engage in a hitherto unknown radical vinylation process through the use of 4-glycosyl-DHP derivatives. This would lead to an efficient complementary method to stereoselectively synthesize vinyl-C-glycosides as classical methods require several steps or transition metal catalysis, and stereoselectivity remains a concern. To our satisfaction, initial reactions with the model galactosyl DHP 6a and VBX 2a were successful, and delivered product 7a in 51% 1 H NMR yield and complete (E)-selectivity, with 5.5:1 dr. Upon reoptimization of the reaction conditions for this substrate class, it was found that reactions in chloroform with Eosin-Y as the photocatalyst gave the best results. Under these new conditions, 7a was isolated in 57% yield (66% 1 H NMR yield) with complete (E)-selectivity and 10:1 dr (Scheme 4).