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The first catalytic cascade reaction of activated isocyanides with para-quinone methide-aryl esters is presented. Catalyst-enabled divergent pathways have also been achieved to deliver skeletally diverse products. While Ag catalysis leads to an unprecedented highly diastereoselective synthesis of tricyclic ketals, a simple procedure employing Cu catalysis produces oxazole-containing triarylmethanes in high efficiency through an unexpected C–C bond cleavage.